Tuesday, May 28, 2024

The 30 Greatest Items of Recommendation for Entrepreneurs in 2022


Right here on The Assessment, we’ve dedicated ourselves to an annual ritual every January — one which doesn’t contain resolutions, however fairly, reflections. 

This yr marks one decade of utilizing the primary week of a shiny new yr as an opportunity to revisit each article and podcast episode we revealed within the 12 months prior. From 2013 to 2023, the purpose of this annual, effectively, evaluate has remained constant: to distill the standout ways down into one actionable information of recommendation. And over time, we’ve discovered it’s a worthwhile train in additional methods than one.

For starters, we hope this concentrated record of can’t-miss-takeaways is helpful to our readers, because it each surfaces the tales you might need missed solely and makes for a helpful refresher on those that beforehand struck a chord.

However these collections additionally function one thing of a time capsule, highlighting the top-of-mind matters and probably the most resonant recommendation in a given yr. For instance, our 2020 version targeted on the shift to digital work and the challenges of main via a disaster, whereas final yr’s compilation nodded to “the Nice Resignation” gripping the headlines, as job-seekers pursued new alternatives, startups notched record-breaking valuations, and funding rounds got here collectively at lightning velocity.

It received’t be stunning, then, that 2022 definitely introduced loads to replicate on. Assembling this yr’s record was a reminder of simply how rapidly issues can change. Amid the layoffs, funds cuts and market corrections dominating the discourse, we strived to convey you the tales that may make a distinction in your day-to-day — whether or not you’re a candidate contemplating early-stage startups for the primary time, a founder trying to get to product-market match extra rapidly, a supervisor trying to help your crew via upheaval, or a frontrunner readjusting your annual plan.

Whereas many are feeling extra uncertainty than ever about what the brand new yr will convey, there are many shiny spots to stability out the scales. Innovation is going down at a fast clip, energizing entrepreneurs in all places. Latest breakthroughs in fields as wide-ranging as AI, nuclear fusion and most cancers therapy are bringing that spine-tingling pleasure that appears like a peek into the longer term.

However oscillating between these extremes of innovation and uncertainty will be disorienting. So whereas leafing via our earlier annual installments (from 2013, 2014, 2015, 2016, 2017, 2018, 2019, 2020, and 2021), we have been on the hunt for a typical thread to function a compass within the months forward. 

Taking a look at the most well-liked recommendation we’ve shared over time, matters appear to run the gamut — from the philosophy of delivering radical candor and the engine that powers product-market match, to the counsel to give away your Legos or the cost to make velocity a behavior. And but readers return to those articles yr after yr, whether or not they’re revisiting or stumbling throughout them for the very first time.

Right here’s our hunch as to why: The perfect company-building recommendation shares a sure timelessness — and a give attention to the basics. Consider it like a pianist taking part in their scales or a professional athlete operating drills. You possibly can’t management what’s going to occur out there. However you’ll be able to management the way you strategy the nuts and bolts of company-building, managing, and private development. 

That hardly means sticking your head within the sand and ignoring traits or what’s most helpful within the close to time period. (So whether or not it’s frameworks for pressure-testing a brand new AI-startup concept, tactic-laden tales on discovering market pull rapidly, or playbooks for constructing with extra effectivity, relaxation assured that we’ll have loads up our sleeves this yr that can assist you meet the second.) 

Nevertheless it does require sustaining a sure stage of perspective and focus. That’s why we additionally pledge to proceed delivering enduring, evergreen recommendation on the startup necessities — irrespective of the local weather.

With that in thoughts, for the tenth yr operating, we’re grateful for the prospect to repeat a well-recognized chorus: We hope you discover relevance and resonance within the following roundup of the 30 finest items of recommendation we revealed this previous yr. Take it with you into 2023 as you retain looking for these shiny spots — and keep targeted on the basics.

There’s loads of content material on the market on the questions managers ought to be asking others, whether or not it’s (shameless plug for our personal items of content material) what to ask in a 1:1 with a direct report, inquiries to ask candidates in interviews, or inquiries to ask their very own managers when managing up

However there’s not almost as a lot recommendation on the questions managers ought to be asking themselves repeatedly throughout key moments of reflection. So we despatched out a name to leaders within the First Spherical group to crowdsource some concepts. The total record made for our most-read article of the yr, however listed below are just a few highlights: 

Who haven’t I heard from? “It is simple to suppose, ‘That individual is so robust, they only care for themselves. I am going to go give attention to the remainder of my crew.’ However I firmly imagine that almost all of my time and training power ought to truly go into people who find themselves high-performing,” says Molly Graham, former COO of BloomTech.

Does the crew know what the technique is? “To be a profitable supervisor, you’ll be able to’t simply depend on doing all of it your self. You need to train your crew to suppose strategically. In case you solely settle for or reject their concepts, your crew by no means learns tips on how to enhance their judgment,” says Wes Kao, co-founder of Maven.

What useful resource suggestion can I ship somebody this month? “I goal to ship my crew members one article, podcast or e-book suggestion each month. It’s been a fantastic software for opening up dialogues on varied matters that we could not get to in any other case,” says Colleen McCreary, former Chief Individuals Officer of Credit score Karma.

Have I requested for assist recently? “Lack of delegation and an incapability to know the place you really add probably the most worth can derail significant development alternatives in your crew, trigger pointless burnout and stress, and finally influence how effectively your organization scales,” says Massella Dukuly, Director of Group Enablement for LifeLabs Studying.

Was I busy or productive at present? “In a startup atmosphere, it’s straightforward to be very busy, however the true problem is discovering methods to be really productive in your work,” says Lattice’s Brett Wienke.

When First Spherical associate and co-founder Josh Kopelman first learn Annie Duke’s bestselling e-book, “Considering in Bets,” he was intrigued by how we might apply her frameworks to our personal work of “betting” on founders. (In case you missed it, final yr, we have been proud to announce Duke as our Particular Accomplice for Resolution-Making Science.)

So it’s protected to say that we have been eagerly anticipating the discharge of her brand-new e-book “Stop: The Energy of Understanding When to Stroll Away.” In her newest undertaking, Duke makes the case for why we have to get higher at quitting — a sensitive subject for founders, who typically worship on the altar of perseverance and grit.

“The issue is that the grit that enables us to energy via will even get us to stay to issues that aren’t worthwhile,” says Duke. “Success comes from sticking to the stuff that’s working and quitting the remaining. That’s why it is advisable to perceive whether or not or not you need to proceed as rapidly as potential.”

To get there quicker, she recommends leaning on this method from Google X’s Astro Teller: “Think about that you just wish to prepare a monkey to juggle flaming torches whereas standing on a pedestal within the city sq.. Teller says to deal with the arduous half first as a result of the whole lot else is simply going to create an phantasm of progress,” she says. 

“In different phrases, don’t begin by constructing the pedestal first. As a substitute, just remember to can truly prepare the monkey to juggle the flaming torches. That is the unknown, the bottleneck. You possibly can definitely construct a pedestal later — in a pinch, you may flip a milk crate the other way up,” she says.

“However when you begin with the pedestal, the time, effort and cash you set into constructing it can begin to create sunk prices. Now your id is extra wrapped up in what you are doing — regardless that it isn’t creating true progress — making it a lot more durable to really give up when you determine that you could’t get the monkey to juggle these torches,” says Duke. “As a substitute, you’ll press on, saying, ‘I simply want to do that another factor, I am so near the breakthrough.’”

That’s why you have to be further cautious once you hear phrases like “Let’s begin by tackling the low-hanging fruit,” at a undertaking kickoff or technique session. “Be sure you’re not simply gathering particles with out truly fixing for the arduous factor first,” says Duke. 

There’s no downside with tackling low-hanging fruit. Ultimately, you need to. However you higher just remember to resolve for the bottleneck first — as a result of each little bit of low-hanging fruit you deal with creates an phantasm of progress and sunk price issues.

Photo of Dharmesh Shah
Dharmesh Shah, co-founder & CTO, Hubspot

To scale your management alongside the corporate, you’ve bought to arm your self with a gentle stream of suggestions — which will be arduous to return by as a founder. That’s why from the early days of HubSpot, co-founders Brian Halligan and Dharmesh Shah invested time in operating one another’s annual evaluations. 

Right here’s how the method works: “Whoever is doing the evaluate picks 15-20 individuals to provide suggestions on how issues are going. It’s the evaluate author’s duty to then synthesize all that suggestions, add their very own evaluation, after which write a 10-15 web page evaluate,” says Shah.

After presenting the analysis packet, the recipient is given house to reply in written kind:

Right here’s what I heard from the suggestions

Listed here are the issues that I’m going to deal with over the subsequent yr.

Listed here are the issues I’m not tackling.

That final one will not be anticipated, but it surely’s a crucial piece of the puzzle. “I typically obtained suggestions that folk didn’t see sufficient of me on the workplace. My response has all the time been that this works as designed. As a super-introvert, two hours of in-person time will zap my power for the remainder of my day,” says Shah. “In case you select to not deal with a selected bug, it’s essential to elucidate why.” 

Right here’s an instance of a bug he did tackle: “I had heard that folk did not actually know what I’m engaged on or what I cared about,” says Shah. To deal with this bug in an introvert-friendly method, he began a collection of inside weblog posts referred to as “Dharmesh’s Ponderings.” “I cowl all kinds of issues I wouldn’t speak about publicly. People can opt-in to learn a weblog submit about what I take into consideration web3 or why we made a selected determination for the corporate,” says Shah. 

As a startup founder, Phaedra Ellis-Lamkins has obtained heaps of recommendation whereas constructing Promise. However one of the resonant items of steering got here from earlier in her profession, when she labored with Prince (yep, the musician). Right here’s how Ellis-Lamkins recalled the story when she joined us on the In Depth podcast:

“Once I labored with Prince, one of many points was that there was monetary stuff that needed to be cleaned up. So I spent lots of time having conversations with individuals who simply wished to spit in my face and thought I used to be the most important jerk ever. I knew I used to be doing the best factor, but it surely harm my emotions,” she says. Ellis-Lamkins referred to as up Prince at some point, and he imparted a little bit of knowledge that also guides her:

You need to resolve when you’re going to play in Madison Sq. Backyard or in your yard. As a result of nobody boos you in your yard. However when you play in Madison Sq. Backyard, somebody’s going to boo you.

“I take into consideration that quite a bit as we construct Promise, as a result of we do each incorrect issues and proper issues. And I remind myself that so long as we’re performing with integrity, I simply need to get used to boos. As a result of the influence I would like is Madison Sq. Backyard — not my yard,” says Ellis-Lamkins.

The company panorama is plagued by jargon that’s all however misplaced its which means from overuse — suppose “net-new,” “low-hanging fruit” or “boil the ocean.” Proper alongside this graveyard of oft-repeated business-speak? Technique.

As a product chief (previously at Tinder and TripAdvisor) and present co-founder of Outpace, Ravi Mehta’s made it his mission to crisp up what it actually means to dive into product technique. He teamed up with Zainab Ghadiyali to create the Product Technique Stack, which encapsulates the corporate mission, firm technique, product technique, product roadmap, and product objectives — bringing these amorphous concepts like “mission” or “imaginative and prescient” into sharper focus. (The message clearly resonated — Mehta’s look on our podcast In Depth was our hottest episode for the yr.)

Illustration of the Product Strategy Stack, in order: Mission, Company Strategy, Product Strategy, Product Roadmap, Product Goals

Mehta’s robust suggestion is to maneuver via every bit of the Product Technique Stack so as. “Targets are on the backside of the stack, not on the high, as a result of objectives ought to come from the roadmap — not the opposite method round. However most of the time, firms say our purpose is to extend retention by 10%, after which the crew will develop a roadmap to attempt to obtain that purpose,” he says. 

He leans on a favourite analogy to (in a way) drive the purpose dwelling. “Let’s say we wish to go on a street journey from Los Angeles to Las Vegas. One of many objectives or KPIs that we’ll have on that journey is the variety of miles pushed — however that is not enough in and of itself for us to achieve our vacation spot,” he says. “We are able to drive 200 miles in the best path — however we are able to additionally transfer within the incorrect path. In each circumstances, we have achieved our purpose, however we have not essentially made progress on the final word consequence that we wished — which is to get to Las Vegas.”

We’ve all felt the signs earlier than. Saying sure when you find yourself already at capability. Feeling so overwhelmed that you just begin to lower out actions comparable to train or alone time. Getting the Sunday scaries — on Saturday. After spending the higher a part of the previous decade learning groups, assembly with specialists and researching the science behind feelings on the job, Liz Fosslien has grow to be an professional herself on recognizing the warning indicators of burnout. (She explored this subject in “Huge Emotions: The right way to Be Okay When Issues Are Not Okay,” her second e-book with co-author Mollie West Duffy.) 

It may be tough for people to muster the braveness to ask for a break, which is why Fosslien says managers should hold an eagle eye out for burnout on their crew. 

Saying you need your individuals to have a wholesome work-life stability is nice, but when their calendars are stuffed with back-to-back conferences, they usually get pinged in any respect hours of the day, likelihood is they received’t really feel protected taking the breaks they want.

Encouraging a tradition of relaxation takes common follow. For instance, to guard an worker’s trip time, think about reprioritizing initiatives they’re part of, or leaping in to complete one thing whereas they’re out. Treating the little issues with the identical attentiveness as life’s greatest hurdles will go a good distance.  

Illustration of a meter showing when we need a break versus when we take a break

Candidates in search of new roles discover themselves competing in a tighter job market as hiring freezes unfold and uncertainty swirls. Understandably, many job-seekers could also be in a mode the place a brand new function at any firm sounds promising. However when you can take a beat, widening the aperture of your search and being as considerate as you will be about your subsequent alternative is of crucial significance.

Nevertheless, significantly for candidates coming from bigger, extra established firms, evaluating the outlook of and potential match with a startup is a frightening prospect. So we requested specialists within the First Spherical group for his or her recommendation on what to search for when evaluating a job and the prospects of an early-stage firm. The full record of ideas is price bookmarking, however right here’s a fast preview:

Assume like an investor. “Working in smaller startups is investing your time — which is probably the most invaluable factor you have got. When contemplating an early-stage startup function, ask your self: Would you make investments your individual cash into this firm and this founding crew?” says Vishal Kapoor, VP of PM and PMM at Affirm.

Turn out to be a pupil of not simply what makes a fantastic product, however what makes a fantastic enterprise. “Typically a flashy product or concept will be fairly catchy, however even at an early-stage startup, understanding the income mannequin is exponentially essential,” says Alexis Zhu, Head of Funds Partnerships at Stripe

Embrace the chance to contribute past your speedy job description. “There are some ‘milestones’ in a giant firm function — individuals administration, promotions, org dimension or scope — which merely do not translate into early-stage startups. It is essential to be open-minded about success wanting completely different at smaller firms,” says Lauryn Isford, Head of Progress at Airtable.

Within the earliest levels of company-building, of us typically worship on the altar of velocity — launch an MVP rapidly, collect buyer suggestions and begin pivoting their method into product/market match. 

However the path to constructing Figma was an train in persistence. Based in 2012, the design startup didn’t truly begin delivery software program to beta customers till 2015. After launch, it took one other two years so as to add paid pricing tiers.

The full story tracing their early GTM path makes for an enchanting learn, however we’ll give attention to one specific element right here: When layering on pricing with its freemium mannequin, the choice on what to gate at Figma’s paid stage took a little bit of trial and error. “The primary time round, we wished to gate the options you want for a design crew, versus what you want as a person designer. So within the first iteration of Figma’s pricing mannequin, the free tier restricted you to solely two customers collaborating on a file collectively, however you bought limitless initiatives. And within the paid tier, you may have many extra of us collaborating on a single file,” says Claire Butler, one of many firm’s first 10 staff and its first enterprise rent.

However this preliminary technique wasn’t fairly working — and, as Butler defined on the In Depth podcast, it goes again to the early crew’s instinct on Figma’s secret sauce. “By limiting the variety of of us who might collaborate on a file within the free tier, we weren’t enabling individuals to expertise the magic second of multiplayer collaboration,” she says. So the crew flipped the script. “We reversed it in order that within the free starter tier, you may solely have a few recordsdata, however you may have a vast variety of individuals collaborating in that file.” 

When you consider gating your product, think about how one can funnel prospects towards your magic second and get them to expertise that as rapidly as potential.

Photo of Brie Wolfson
Brie Wolfson, previously of Stripe & Figma and present founding father of Constellate

“On the finish of the day, the one factor that truly issues is the influence our work has on our firm, our prospects, our colleagues, and our skilled growth. And the one technique to keep on high of that is to carry ourselves accountable to our higher-order objectives with as a lot enthusiasm as we have now for the dopamine rush of reaching inbox zero.”

Brie Wolfson has labored for tech firms of all sizes and styles, together with family names Figma and Stripe, so we’d advocate listening to her on this one. 

Today she’s bought her arms full constructing Constellate, however final yr, Wolfson took the time to share her private assortment of docs and templates for staying targeted within the day-to-day, whereas nonetheless making progress in the direction of broader objectives longer-term. There’s a lot tactical goodness to be discovered that we extremely advocate borrowing her toolkit in full (and subscribing to this calendar to include these workout routines into your workflow).

However we’ll spotlight one specific template right here: As a quarterly train, Wolfson suggests sitting all the way down to write a press launch — not a couple of new product launch, however about all of the issues you shipped and the influence they’re having.

Whether or not it’s a part of efficiency evaluate season otherwise you’re trying to interact in deeper reflection as the brand new yr will get underway, the timing couldn’t be extra good to take this one on. Right here’s her suggestion on what to incorporate (and a helpful template for crafting your individual):

Headline/Lede: the eye grabber

One-line abstract: think about how somebody would describe this to a colleague

High 3-5 belongings you shipped

The place your time went

Key insights or learnings 

Progress on metrics

Qualitative impacts

Contributions to the broader crew/firm

Suggestions you obtained from stakeholders/customers (inside or exterior)

One piece of artwork (graph, image, screenshot, and so on.)

Total temper/sentiment

Something the broader group did that you just want you may have been part of

What you’re actually happy with

Something you’re not so happy with

A glance forward: What you’re delivery subsequent, what you’re enthusiastic about, huge alternatives for you, your crew, or your organization, and any foreseen blockers, dangers, or belongings you’re fearful about.

“As managers, our default setting is to leap in and sort things when a state of affairs goes sideways. ‘I do know the reply, and I want to inform them,’ is a typical mentality. However over-relying on fixing constrains our potential to steer and robs our crew members of development alternatives,” says Anita Hossain Choudhry and Mindy Zhang, who’ve coached lots of of executives by way of The Grand and Throughline.  

They’ve noticed that the most important rigidity for managers occurs once we use our “personal compass” to information our crew — or fairly, rely an excessive amount of on our personal previous experiences to advise direct reviews via their distinctive challenges. “Being the hero who swoops in and relieves somebody of their issues feels good, and it’s arduous to let go of the prospect to bolster our competence,” they are saying.

As a substitute, Choudhry and Zhang advise placing in your teaching cap. “To place it merely: Teaching is a talent, whereas being a supervisor is a job. The important thing aspect is that you just’re attempting to faucet into their knowledge, not yours.”

Two foundational expertise they advocate for getting began are working towards empathetic listening and asking open and sincere questions. Begin by shifting from the extra pure self-focused listening mode (“What does this imply for me?” or “How do I assist them determine this out?”) to empathetic listening (“What is going on on for this individual?”). Subsequent, be careful for a bent to ask closed questions like, “Have you considered doing X to resolve the issue?” which limits the set of potentialities for the opposite individual to reply with. (Choudhry’s and Zhang’s helpful chart under gives up another alternate options.)

Chart showing the difference between closed and open questions

As a four-time founder (and present CEO of Ranges), Sam Corcos is relentless about optimizing his time. Far too typically, he sees of us reluctant to delegate as they transition from builder to chief — but it surely’s one of the crucial expertise to get proper.

“In ‘The 4-Hour Workweek,’ one line from writer Tim Ferriss caught out to me: ‘By no means automate one thing that may be eradicated, and by no means delegate one thing that may be automated or streamlined. In any other case, you waste another person’s time as an alternative of your individual, which now wastes your hard-earned money,’ says Corcos. 

Right here’s a tactic he leans on to get rid of busy work, fairly than delegating to help workers or utilizing engineering time to automate it: 

Earlier than you think about delegating or automating a job, it’s all the time price interrogating whether or not that job is price doing within the first place. There’s nothing worse than spending time bettering one thing that ought to by no means have existed to start with.

A tactic to attempt is the “anti-pilot”: eradicating the characteristic and seeing if anybody notices. “In case you don’t get lots of complaints, it’s a robust indicator that the characteristic wasn’t including as a lot worth as you thought,” says Corcos. 

“A current instance is after I thought-about including a recurring job for an EA to remind individuals to place collectively a weekly recap for his or her perform (which takes about 2 hours). However as an alternative, I requested the useful results in chorus from posting their updates for a few weeks to see if anybody observed. It turned out that it was a nice-to-have, however actually didn’t add that a lot worth, so we killed that undertaking,” he says.

Ximena Vengoechea is a grasp within the artwork of listening. As a seasoned consumer analysis chief, she’s led and noticed 1000’s of interviews at firms like Pinterest and LinkedIn. She’s even written a e-book on the topic, publishing “Pay attention Like You Imply it: Reclaiming the Misplaced Artwork of True Connection.” 

One space that’s ripe for refining your listening recreation is the usual 1:1 conferences between managers and direct reviews — primarily as a result of it’s straightforward to fall into a well-recognized rhythm right here. 

“As you construct a relationship together with your direct report over time, it’s essential to concentrate to patterns. For instance, in remedy, shoppers typically convey up an important factor within the ultimate jiffy of a session — it’s referred to as a doorknob remark. Proper earlier than you begin wrapping up, you say the factor that you just truly wished to say the entire time, however wanted the whole hour to muster sufficient braveness. And we generally see an analogous factor in 1:1s,” says Vengoechea.

Ending conversations on a doorknob remark signifies that these discussions by no means stray too removed from the floor, and the uncomfortable challenges are left unexplored. 

In case you’re a supervisor trying to deepen the conversations you’re having together with your direct report, attempt asking this one query: “What would you save for the tip of our 1:1 at present? Let’s begin with that.”

On the flip aspect, Vengoechea encourages direct reviews who’re fighting feeling heard to think about using clear and easy language to be as direct as potential with managers. “Usually, we predict we’re expressing our wants clearly and we’re truly speaking round them. Essentially the most direct path to being heard is to speak our wants explicitly.” 

Photo of Liz Kofman-Burns
Liz Kofman-Burns, co-founder of Peoplism

Co-founders Amber Madison and Liz Kofman-Burns construction their hiring course of a bit unconventionally. Earlier than each interview, candidates for Peoplism, a data-driven DEI consulting agency, obtain a prep information outlining the hiring timeline, wage — and the questions they’ll be requested within the interview.

The thesis behind this atypical strategy is to make their interview course of as inclusive as potential, given what number of behind-the-scenes components contribute to somebody nailing on-the-spot interviews. 

“Being nice in an interview setting will be the product of going to elite faculties, realizing individuals in the identical occupation, and even gaining access to somebody who’s already working on the firm to prep beforehand,” Kofman-Burns says.“On-the-spot interviews consider a sure set of standards — however is that the standards that you just’re actually in search of within the function?” 

If you wish to consider candidates for clear competencies, you wish to give them the most effective shot of truly displaying you whether or not or not they’ve these expertise. In case you don’t give candidates a way of what you’re going to be probing, you find yourself hiring of us who’re simply the most effective at interviewing.

Giving of us time to prep for the questions prematurely additionally faucets into what it’s truly like working in most startup roles. “The way in which we arrange the interview mirrors the true world, the place you’re capable of truly put together for what you’re anticipated to perform,” says Madison. “If you give of us the chance to evaluate the interview questions prematurely, it raises your expectations of the standard of the solutions you get again.”

Amber Madison, co-founder of Peoplism

As when you didn’t get sufficient grief already out of your dentist, Russ Laraway has another factor so as to add to your to-do record: follow managerial hygiene. 

In his e-book revealed final yr, “When They Win, You Win,” Laraway shares classes he’s collected after 20 years of managing individuals in a number of completely different environments (as an govt at Twitter, Chief Individuals Officer at Qualtrics, a startup founder and an organization commander within the U.S. Marine Corps, to call just a few.)

In his analysis, Laraway discovered that reminding your crew of firm objectives (and connecting the dots with how their work is contributing to them) is intently aligned with increased worker engagement. It’s additionally one thing that managers need to work on repeatedly. 

To kickstart good habits, incorporate the following pointers in your subsequent assembly:

Set a cap on priorities to supply readability. Ask every crew member to articulate their three priorities — and be actually strict about sticking to 3. “Don’t let this flip into an arms race the place somebody begins itemizing 4, and one other then lists seven. This train isn’t about getting visibility into each single factor of us are doing. That is about doing the arduous enthusiastic about probably the most essential factor of us have to get performed at present or this week,” says Laraway.

Add this phrase to your repertoire to proceed to bang the drum of what issues most. “Ask the query: Which quarterly purpose does that workstream help? In case you hold discovering that the work that you just’re doing isn’t mirrored within the quarterly objectives, it’s time to rethink the way you’re approaching these OKRs, or get them proper the subsequent time,” Laraway says.  

On high of serving to us scale back bias and convey much more rigor to our personal investing course of, Annie Duke additionally shares her recommendation with founders and angel traders, each in closed periods for the First Spherical group and on this tactical decision-making information on The Assessment — so we’d be remiss if we restricted her to only one tip on this record.

There have been so many glorious psychological fashions (summarized within the chart under), however we’ll give attention to quantity three: getting group suggestions in an unbiased method.

Image: Annie Duke's Mental Models for Decision-Making

It’s nice to produce other individuals make the identical judgments as you to uncover the place there’s dispersion of opinion— however that solely works if the judgments are impartial,” says Duke. “In a bunch, persons are going to attempt to persuade one another. There’s going to be contagion, and generally it might probably even grow to be combative, which is unhealthy for decision-making.”

That’s why it’s crucial to gather suggestions asynchronously and independently. “That method, you’ll be able to see everyone’s opinion and pinpoint the locations the place opinions don’t align. I favor to make use of ‘dispersion’ over the adverse connotations of ‘disagree’ — it’s a extra impartial method of speaking about locations the place individuals’s opinions differ,” she says.

Listed here are just a few ways to check out:

Have crew members write down their opinions anonymously on a digital whiteboard. Or when you’re in individual, have them write it on a chunk of paper to move alongside so another person can learn their take. 

If of us in your crew are sharing their very own opinions aloud, go in reverse order of seniority.

When sending an e mail asking for suggestions on an concept, ask everybody to e mail you instantly as an alternative of replying all. Then mixture the outcomes and share out. 

Because the founder of individuals administration platform Lattice, Jack Altman definitely is aware of a factor or two about powering profitable groups. On In Depth, he shared tactical recommendation for assembling govt groups particularly — a problem that by no means fades, whether or not you’re within the earliest levels of figuring issues out, or the later levels of scaling the enterprise.

​​I’ve heard the analogy that constructing your organization’s management crew is form of like portray the Golden Gate Bridge — by the point you get from one finish to the opposite, you need to return and begin repainting as a result of a lot has modified,” he says.

Listed here are two of Altman’s ideas for ensuring you discover the best match:

Pay attention for possession language: “That is a type of trite issues everybody talks about, however you actually do want to search out leaders with a deep possession mentality. That mindset comes via within the language individuals use and what they give attention to when answering interview questions,” says Altman. “Of their final one or two roles, I wish to dig in by asking issues like, what have been you introduced in to do? How did it evolve over time? Inform me about a few of the huge initiatives. What have been the most important successes you had? What have been the issues that did not go the way in which you wished? Simply repeatedly asking why and what, pulling on these threads many, many occasions. Are they self-reflective about what they’ve realized, or is there a mentality of, ‘We did not have the funds,’ or ‘The founders have been setting issues up for failure’?”

Verify your references: “I spend lots of time on references, leaning on them fairly extensively. However you need to take issues with a grain of salt. And generally you need to — this may sound a little bit loopy — do references on the references, like once you get a complicated reference the place you’ll be able to’t piece a narrative collectively,” says Altman. “There are circumstances the place I’ve performed a reference with one other founder about an exec candidate, and it would not make sense to me as a result of each different reference was good. However after doing references on the references, I realized that possibly that founder was a tough character, or the candidate was truly being tremendous respectful after they have been describing how they left the corporate.”

Photo of Meka Asonye
First Spherical’s Meka Asonye

As a first-time founder simply beginning out, it may be difficult to pivot from architecting the product to growing a method for promoting to prospects. 

Earlier than becoming a member of First Spherical, Meka Asonye lower his tooth at Stripe because it scaled from 250 to 2000 individuals and matured its gross sales org. He later served as VP of Gross sales & Providers at Mixpanel, operating a 100-person world income crew, so he’s the proper sounding board for extra technical founders who’re simply dipping their toe into founder-led gross sales. 

Too typically, Asonye sees founders attempting to chase too many people directly with their product. “​​The frequent failure mode I see is somebody simply needs to get to 5 prospects, or a founder is keen to hit $100,000 in ARR, so they’re having a dialog with everybody beneath the solar,” Asonye says. 

I’m all the time telling founders I work with to do much less, or do extra for fewer individuals. Get to the red-hot core of who you imagine your buyer is, and you may work your method out from there.

So within the early days, go slim, not broad, together with your ICP (perfect buyer profile). “Founders ought to be capable to say what their buyer seems like, the place they hang around, what issues they’ve, how huge their firm is, and the way you are going to promote to them,” Asonye says. “You possibly can have a ravishing product, however in case you are promoting it to the incorrect viewers, it’s going to appear to be you have got a horrible one.” 

“If you’re a excessive performer, the extent of the suggestions you usually obtain is, ‘You’re doing nice!’ And whereas that makes you’re feeling good within the second, it’s not truly useful in the long run,” says engineering chief Amber Feng, one of many first dozen hires at Stripe.

“I take into consideration if I used to be an Olympic gymnast or an NBA basketball participant and I requested my coach how I used to be doing. If all they instructed me was, ‘You’re doing nice!’ I’d in all probability fireplace them. Your whole job as an elite coach is to provide brutally sincere suggestions — inform me what I can do to enhance, even incrementally.” 

We wish to be world-class Olympic athletes in what we do — and we want brutally sincere suggestions to get there. 

In the case of doling out impactful suggestions for top performers, on the In Depth podcast Feng beneficial beginning with the report’s profession objectives. In case you don’t know what of us are hungry for, you’ll battle to provide them helpful suggestions. “If I’ve a star engineer on my crew who needs to grow to be a founder, hastily, I’ve so many concepts for them. The suggestions in all probability received’t solely be about bettering their code high quality — it can even be about what they’ll do to tackle extra management with certainly one of our huge enterprise strains,” she says.

Amber Feng, former Stripe engineering chief

Earlier than beginning Maven, Gagan Biyani co-founded Udemy (a web based schooling firm), began Sprig (a meal supply startup), and was early at Lyft. Common readers may also acknowledge his title from the unbelievable Minimal Viable Testing framework he shared right here just a few years again. Constructing on this different strategy to the standard MVP course of, he stopped by In Depth final yr to share a preview of the corporate formation recommendation within the ideation bootcamp course he runs with Sam Parr.

“One of many extra frequent errors entrepreneurs make when beginning an organization is failing to contemplate all of the assorted enterprise fashions earlier than deciding which one to pursue,” says Biyani. “It sounds quite simple. Nevertheless it’s superb what number of entrepreneurs begin an organization with a enterprise mannequin already baked in from the start.” 

Take the extra particular concept of a peer-to-peer market for gardening provides, with of us renting unused provides to their neighbors. “I can take that concept and cut up it up into 5 or 10 completely different concepts. What if as an alternative of renting, you’re promoting them? What if I supplied a rental service the place you’ll be able to hire gardening tools from a centralized location? What if it was a gardening tools e-commerce firm? What if I made a decision to invent higher gardening tools than what exists at present?” 

In case you do not suppose via all these various factors, likelihood is somebody on the market within the market of concepts goes to provide you with the best reply — however you did not spend the time to determine the entire choices, so that you have been useless on arrival from day one.

Listed here are his recommendations for whittling down your record: “TAM is clearly one of many greatest drivers of whether or not or not you have got the best enterprise alternative. One other method is to contemplate which one’s the best to get began tomorrow — it isn’t sufficient, but it surely’s useful,” says Biyani. 

“However one other method is if all three concepts existed, which one would win in a contest? Whereas I used to be proper in regards to the meals supply market with Sprig, we picked the incorrect mannequin. Sprig was a greater expertise than DoorDash or Postmates for a very long time, and we have been gaining market share — till Uber Eats got here in and fast-forwarded our eventual demise. Our enterprise was working when rivals have been basically unoptimized and never at maturity but. What I did not ask myself was what is going on to occur 10 years from now when their enterprise is working? And it is the most effective model of their buyer expertise versus their present model? How is that going to compete with my concept?”

Photo of Melissa and Johnathan Nightingale
Melissa and Johnathan Nightingale, founders of Uncooked Sign Group

It’s presumably probably the most dreaded a part of any management coaching — seize a associate and act out a situation that demonstrates some administration tactic, like giving tough suggestions to a direct report. Along with being simply plain awkward, Melissa and Johnathan Nightingale, founders of Uncooked Sign Group, don’t discover role-playing to be of a lot use. 

Individuals typically suppose they don’t like administration coaching. However what they’re actually saying is, “I don’t like shitty administration coaching.” That’s completely different from saying, “I don’t take pleasure in studying new expertise that make me higher at my job.”

As a substitute, the duo advises creating an area the place managers really feel protected speaking in regards to the precise struggles they’re having. Listed here are two ideas for laying the groundwork for weak, impactful conversations: 

Arrange the house: “We’re huge followers of Priya Parker’s e-book, ‘The Artwork of Gathering,’ together with her mannequin for setting guidelines of the house. That features clarifying what confidentiality means within the session and asking everybody to decide to it. This creates a protected house the place of us can present up otherwise than of their day-to-day,” says Melissa. 

Go first: “The analysis is fairly clear that there’s reciprocity to vulnerability — they’ll go deeper when their colleagues do,” says Johnathan. “For instance, I typically inform the story in regards to the first time I needed to fireplace somebody and the way I bought so wired that I threw up within the car parking zone afterward.”

The early days of any startup seem to be a mad sprint to get a tough model of the product out into the world as rapidly as potential. Andrew Ofstad and his co-founders definitely felt this strain again in 2012 after they have been tinkering with the concept that would go on to grow to be Airtable. “On the time, it was all in regards to the Lean Startup, getting early buyer validation and failing quick, placing out an excellent tough prototype to get to know the client after which rapidly pivot,” he says.

As a substitute, they targeted on tackling the primary danger for the corporate as early as potential. “For us early on, that was, ‘How will we truly make this database accessible to non-programmers?’” says Ofstad. “That meant it was all about making it straightforward to make use of, iterating on a prototype and getting plenty of suggestions. It appeared like launching the product publicly would not actually get us extra information or speed up the trail to our purpose. We needed to separate the idea of attempting to get suggestions from prospects and refining the product from the idea of a public launch.”

Right here’s what that seemed like for Airtable: “Our technique was to construct a really horizontal product after which roll it out to extra individuals over time. Very early on, we had a non-public alpha. It was invite-only, however you may refer different individuals, in order that helped us get some natural development, however not a ton,” says Ofstad. “After possibly 100 individuals or so, finally we felt like we have been in an excellent place.” This took two years, he says, which is why it’s key to loosen your expectations round what your MVP “ought to” appear to be. “We needed to construct so many options to get to one thing helpful. The MVP for our product was not anyone factor.”

Photo of Andrew Ofstad
Andrew Ofstad, co-founder of Airtable

“The important thing factor that leads individuals to really feel like firms are slowing down is when choices do not get made., when there is a chance or a problem and it simply drifts on. Not realizing who can decide is the curse of huge organizations,” says Sara Clemens, former COO of Twitch.

At massive companies, making choices is commonly not a matter of getting any individual to say sure, it’s getting no one to say no.

As she defined on the In Depth podcast, as a startup begins to scale past a small group of founders and early staff, of us should sketch out determination rights to remain agile: “As COO, my function was to diagnose the place there have been choices that weren’t clearly allotted to somebody within the enterprise. What I imply by determination rights is simply actually who can resolve the factor? Who can resolve whether or not that may be funded? Who can resolve whether or not or not we’re going to evaluate a buyer question and make a change in coverage primarily based on new info? Who can resolve whether or not we do a advertising marketing campaign in Brazil?” she says.

Arielle Jackson has had a hand in shaping lots of of startup manufacturers, whether or not it’s serving to firms like Patreon, Loom, Bowery and eero architect their positioning and branding behind the scenes, or her earlier product advertising work launching and rising marquee merchandise like AdWords, Gmail and Sq. Stand.

She shared heaps of branding recommendation on The Assessment final yr, however we’ll give attention to one of many extra frequent positioning pitfalls she’s noticed: founders’ tendency to emphasise their product’s emotional advantages over the useful ones. Taking pictures for the subsequent pithy “Assume Totally different” or “Simply Do It” tagline is placing the cart earlier than the horse, she says.

“As Matt Lerner identified in his language/market match Assessment piece, Nike and Apple earned that proper to be elusive over many years. However once you’re an progressive little startup, you have not but. You want to be actually clear and useful till individuals perceive what you do,” Jackson says. “Problem your self to say, ‘What’s the most bare-bones, useful method I might phrase this?’” She shares just a few examples as inspo:

“I labored with Loom and we landed on ‘Report immediately shareable movies of your display screen and cam,’ which is precisely what they do.”

“I labored with Rupa Well being via First Spherical, whose profit is, ‘Order, monitor and get outcomes from 20 lab firms in a single place.’”

“Peloton’s early headline actually stated, ‘Be a part of studio biking lessons from the consolation of your property.’ That was the useful profit they wanted to bolster earlier than they might keep stuff like, ‘Collectively, we go far.’”

To remain laser-focused on the useful, Jackson suggests one other easy train: “Within the story of Cinderella, what’s the tremendous useful factor that occurred? She had a fairy godmother who turned her pumpkin right into a carriage. On the emotional aspect, she lived fortunately ever after. And proper within the center — she married a prince,” says Jackson. 

Run via an analogous brainstorm as you’re enthusiastic about advantages. “Checklist all of the useful, easy advantages you have got, all of the emotional advantages you have got, and all those in between. Attempt to keep targeted extra on the useful aspect of the ledger,” she says. 

Particularly when you’re establishing a brand new class, you need to be sure that individuals perceive what the hell it’s you are speaking about earlier than you’ll be able to transfer increased up Maslow’s hierarchy in your messaging.

In case you’re desperate to study extra from Jackson firsthand, we’d extremely advocate her cohort-based course powered by Maven.

Photo of Cristina Cordova
Cristina Cordova, early Stripe and Notion worker and early-stage investor

After becoming a member of as Stripe’s twenty eighth worker, serving as Notion as Head of Platform & Partnerships, and advising founders as an early-stage investor, Cristina Cordova has assembled a powerful assortment of classes on constructing and scaling startups —  one thing we have been desperate to faucet into after she got here aboard First Spherical final yr. Right here’s one gem that stood out:

Elad Gil talks about ‘hole fillers,’ and I’ve all the time thought it’s the proper phrase. Stripe was rising so quick that we would have liked individuals to plug holes within the group,” she says. “That’s why you want to join the aspect jobs. My core focus at Stripe was on partnerships, however I all the time had obligations on high of that. At one level, an engineering supervisor left, so I took over managing the crew. I additionally led DEI initiatives for over a yr earlier than we made a full-time rent,” says Cordova. 

“These alternatives allowed me to construct a status and gave me extra publicity to different features for my very own growth. Promotions typically require work that has cross-org influence, which these sorts of initiatives can assist with,” she says. 

Nevertheless it’s not nearly padding your individual resume. “It’s very straightforward to fall right into a mindset the place you’re criticizing all of the issues that aren’t going effectively — it’s a lot more durable to provide you with a proposal for making issues higher. Are you continuously wanting round to search out new methods to assist the individuals round you? As a substitute of being tremendous pissed off by how busy your supervisor is as of late, is there one thing you may do to assist them get extra leverage?”

It’s important to develop with the corporate — fairly than having the corporate develop round you.

“Loads of early-stage staff grow to be the heroes of the corporate. They construct lots of options, resolve main outages and provide you with novel methods to enhance the infrastructure. As the corporate grows, extra of us are available in and, with out issues written down, that previous guard will get bombarded with questions,” says David Nunez, an early docs chief for Stripe and Uber. “Immediately, the entire worth these early heroes delivered initially, which was constructing and delivery, they now have a lot much less time for.”

That’s the place sharp inside documentation is available in. However it’s possible you’ll be shocked that Nunez’s essential piece of recommendation on the subject of inside docs isn’t to essentially exit and rent somebody to repair the issue for you. “I’ve realized that, particularly in high-performance environments, altering the tradition is the very best leverage funding you may make,” he says. 

You’ll see significant progress rapidly when you first tackle incentives and rewards for writing and sustaining documentation — or lack thereof.

Listed here are just a few ways for making a tradition of documentation:

Make it part of the job ladder: “I’ve discovered that when you codify knowledge-sharing expectations in job descriptions and job ladders, of us will inherently look to meet these obligations on their ladder.”

Shine a highlight, even outdoors of efficiency evaluate season. “One supervisor included their ‘doc star of the week’ in every weekly replace she despatched. It’s such a straightforward factor to simply name individuals out, and folk like to be acknowledged — particularly for doing one thing outdoors of their consolation zone.”

Carve out the time. He’s additionally seen different groups do “docs bashes” (like bug bashes) the place the entire crew will spend a day, or perhaps a week, simply engaged on documentation. “Make a leaderboard and see how motivated engineers get to contribute.”

As a monetization chief and pricing advisor, Dee Sahni sees individuals attempt simple arithmetic to enhance their unit economics: increase costs = extra lifetime worth. As a substitute, she coaches of us to strategy pricing with a extra bespoke method for better longevity, transferring away from one-size-fits-all and in the direction of granularity.

Highly effective monetization would not take away from buyer expertise. It rides on it. In the most effective circumstances, it improves the expertise. Considerate monetization may even scale back costs.

To reveal this, she sketches out some concepts for amplifying high-performing cohorts with customized pricing. 

Illustration amplifying a positive impact cohort

“When a cohort is over-performing, (like a high-retention, high-LTV cohort), you’ll wish to amplify its influence by growing the cohort dimension, or growing retention — or each,” says Sahni. Frequent ways embody:

Enhance cohort dimension with decrease costs, bettering conversion charges: “Growing the dimensions of a high-retention cohort will drive common retention up. For example, many firms enhance the dimensions of excessive retention cohorts by providing decrease costs for longer subscriptions.”

Enhance cohort dimension via higher characteristic units and higher conversion charges. “Amazon Prime grows the dimensions of its high-retention cohort by providing the free deliveries characteristic.” 

Delight these prospects to additional enhance retention and repeat purchases. “Loyalty packages, reductions and rewards are straightforward methods to indicate these prospects they’re valued. Nordstrom is famously identified for its stellar customer support as a way to retain high-value prospects. Equally, Wayfair gives members-only reductions to bolster loyalty.”

Photo of Dee Sahni
Dee Sahni, VP of Product at Figment and startup advisor

As the previous Senior Director of Expertise Acquisition, Shreya Iyer spent 11 years at Splunk, rising her profession alongside the analytics automation platform. As one of many firm’s early Expertise hires, Iyer is especially obsessive about employer branding. She’s experimented with dozens of ways over time as she’s watched Splunk’s personal model develop and alter from scrappy upstart to publicly-traded BigCo. 

Even when your startup doesn’t have a completely shaped model but, it’s a lot simpler to see the substances of your organization tradition with a headcount of ten versus 100. Iyer says this can be utilized as your differentiator when hiring candidates. And it doesn’t must be critical. 

“Earlier than anybody knew what Splunk was, they’d in all probability seen the corporate on our swag. We had a penchant for humorous t-shirts, with phrases like ‘Take the SH out of IT,’ or ‘I like Huge Knowledge and I can not lie.’ Perhaps of us rolled their eyes a bit, however they remembered us,” says Iyer. 

It was embracing these quirky, humorous traits early on that finally made Splunk stand out. “One in every of our founders, Eric Swan, would make feedback in interviews that Splunk was truly only a t-shirt firm that occurs to promote software program. The corporate actually embraced that humility as a part of our character, and that low-ego tradition shone via in our interviews with candidates,” she says.

Within the early days of product-building, the transition from inside dogfooding to placing your product out in the true world generally is a sizable leap — that’s the place design companions can assist cushion the autumn. However when attempting to enroll design companions for enterprise infrastructure product Cockroach Labs, Chief Product Officer Nate Stewart didn’t precisely have of us lining up the door to be early testers.

His recommendation to different product leaders dealing with related headwinds is to bucket your design companions into completely different classes: 

Strategic Design Companions: “With these of us, we talked about the place we thought the database market was going. What have been a few of the macro issues that individuals have been experiencing and the pains that their group was going via?” 

Roadmap Design Companions: “These have been individuals offering suggestions on the precise roadmap and the capabilities that we wish to add to the database. For instance, it was clear over time that if persons are putting in a mission-critical database, they need it to plug into the remainder of the group and ship updates to different methods in real-time. So we talked about including a real-time information streaming functionality to the roadmap — there was lots of pleasure round that and the design companions helped us de-risk the engineering funding it might take to construct.”

Characteristic design companions: “That is probably the most tough design partnership, which is getting engineers to attempt specific options. These are the design companions who really feel probably the most ache that your product can resolve. For instance, we had an early buyer doing a major quantity of cost processing, and all of that was taking place in a single information middle. If that information middle went down for any motive, their enterprise can be fully offline. They needed to construct a extra resilient system, they usually have been prepared to speculate a few engineers to ensure that Cockroach would assist them evolve to a cloud-native structure.” 

MBA-style reviews about market dimension are nice. However once you begin to see the conviction out of your design companions, you get an image not simply academically of how huge a market is — you begin to really feel it viscerally. 

Photo of Nate Stewart
Nate Stewart, Chief Product Officer, Cockroach Labs

A part of what makes a startup’s gravitational pull so robust for its staff is the values. Earlier than even touchdown on a tangible product concept, founder Laura Del Beccaro was obsessive about firm tradition — squirreling away bookmarked reads, inspiration and concepts for the tradition she dreamed of constructing. 

However crafting a shared system of beliefs isn’t a one-and-done train for firms simply beginning out. “Every time there’s an inflection level at your organization — a fundraise, a giant market shift, a method shift, a change in management, a layoff — these are all good occasions to re-evaluate,” says Del Beccaro. “ What issues do you wish to maintain onto or change as you scale?”

To kick off this cultural pulse verify, Del Beccaro gives a brainstorm (as a part of a five-step framework) for the way firms of any dimension can re-group and re-evaluate the tradition: 

For co-founders simply beginning out: Ask yourselves questions like, “It’s 5 years down the road, and everybody is definitely dwelling out the values we chosen. What would an organization that we’d be happy with appear to be?” or “In case you took 6 months off, and left no instructions apart from ‘Comply with our values to a T,’ would you be pleased with the end result?”

Early-stage firms: “In case you’re nonetheless on the small aspect, have everybody on the firm take into consideration the qualities in leaders or direct reviews that they’ve valued up to now. Then get every individual to reply two questions: ‘What do you imagine are the at present held values of the corporate at present?’ and ‘What values would you wish to see our firm undertake?’” 

Later-stage firms: In case you’ve bought lots of of staff already, do that variation: “Create a manageable variety of ‘cultural ambassador’ teams, pulling people who opt-in throughout groups, ranges, and backgrounds to run their very own separate brainstorms and current their findings in a templated format. Then use a software like Dovetail to search out traits,” says Del Beccaro.

After becoming a member of Ranges in her first-ever Chief of Workers Function supporting co-founder Dr. Casey Means, Sonja Manning discovered that she rapidly ended up with a to-do record miles lengthy. To deal with the combo of brief and long-term priorities, she developed a five-part system that people could wish to borrow for conserving all of the balls within the air:

Every day to-do lists organized into classes: learn, write, suppose. “This helps me set an achievable plan for the day and the week. On the finish of every single day, I’m going again via and jot down how lengthy every factor truly took me to finish, which gives the chance for an on the spot transient reflection.”

A weekly and month-to-month priorities doc the place we monitor the chief’s weekly 3-5 priorities and 5 month-to-month priorities. “This, together with our calendars, turns into a retrospective for what was achieved in per week.”

An ongoing dialogue doc with a operating record of things. “Gadgets get checked off after they’re mentioned or accomplished. This reduces cognitive burden as a result of the whole lot has a spot and lives there till it’s performed.

Calendar displaying when the work will occur. “As an aspirational, ‘Rome might be inbuilt a day’ sort of individual, monitoring precisely when I’ll accomplish duties on calendar blocks is important in conserving me sincere about what I can obtain in a workday. Usually, if I’ve blocked a job for 60 minutes and after 60 minutes it’s not performed, I’ll both ship the model I’ve or re-scope the duty.” 

Monitoring duties in your calendar is a good forcing perform for delivery work that’s less-than-perfect (as a result of, on the subject of startups, good is the enemy of fine).

High illustration by Alejandro Garcia Ibanez, that includes (from left) Sam Corcos, Phaedra Ellis-Lamkins, Annie Duke, David Nunez, Ximena Vengoechea.



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