How should a manager test whether an underperforming employee can be salvaged?

Kevin Systrom · Feb 22, 2023

The real difficulty for founders is not trusting people but moving quickly to make a change when a hire isn't working, and second-time founders do this where first-time founders struggle

He tried it several times in the past 18 months and regretted the occasions when he didn't move fast; it's a lesson relearned repeatedly while running a company

Scope: must be done as a compassionate leader who first tries to help the person be great

40:48 20VC: Instagram Founders Kevin Systrom and Mike Krieger on Why Social Networks Should Be Less Social & The Next Wave of Social | Why San Francisco Will Return with a Vengeance and The Future For Remote Work | Let's Get Personal: Relationships to Money, Be

Mike Krieger · Feb 22, 2023

Recognizing that a role isn't working and moving on quickly is the genuinely empathetic action, even though it runs against basic human instinct

A first-time founder's instinct is that compassion means having a fifth conversation to force it to work; the second time you see the empathy lies in acting

42:28 20VC: Instagram Founders Kevin Systrom and Mike Krieger on Why Social Networks Should Be Less Social & The Next Wave of Social | Why San Francisco Will Return with a Vengeance and The Future For Remote Work | Let's Get Personal: Relationships to Money, Be

Mike Krieger · Feb 22, 2023

Tolerating a talented but wrong-fit person never works — you should cut it off early, accept a week or two of slowness, and then move forward faster

He keeps relearning this lesson: it doesn't work, and the short-term slowdown from cutting is worth it

51:08 20VC: Instagram Founders Kevin Systrom and Mike Krieger on Why Social Networks Should Be Less Social & The Next Wave of Social | Why San Francisco Will Return with a Vengeance and The Future For Remote Work | Let's Get Personal: Relationships to Money, Be

TJ Parker · Jun 5, 2023

Once he concluded a hire wasn't working he made the call immediately rather than giving them more time

He was generally an impatient operator, so he didn't dilly-dally; the only delay was because the conversations are hard

Scope: frames his impatience as his biggest flaw

13:26 20VC: The Largest Venture Backed D2C Consumer Exit; PillPack: $0-$300M Revenues in 5 Years & The Biggest Lessons Scaling the B2B Business to $300M in 2.5 Years with TJ Parker, Co-Founder @ PillPack

Fabien Pinckaers · Feb 12, 2025

His biggest people mistake is firing too late, and founders should fire sooner — by the time you think negatively about someone it is already too late

Entrepreneurs are necessarily optimistic and keep believing things will improve, so the moment doubt turns into negative thinking the decision is overdue; when there is a doubt, there is no doubt

37:11 20VC: The $5BN Company Built from the Belgian Countryside | The Story of Odoo: The Company with No Plans to Sell, IPO & Their Billionaire Founder Who Does Not Care About Money with Fabien Pinckaers, Founder & CEO @ Odoo

Kyle Norton · May 30, 2025

For traits you consider uncoachable — values and work approach — you should terminate almost immediately rather than wait

He cut someone on day 11 for not bringing good energy; if someone is already rude or flippant to an enablement leader during onboarding when they should be on best behavior, it will only get worse later

Scope: limited to non-coachable traits like values and attitude

14:26 20Sales: From $2M ARR to $40M ARR: The Playbook | How to Use AI To Supercharge Your Sales Team | Why Pipeline Reviews are BS | The Sales Call Script that Closes 99% of Prospects and How to Hire the Best Sales Reps with Kyle Norton, CRO @ Owner

Mati Staniszewski · Sep 8, 2025

If you are unsure about a hire in their first weeks or months, you should separate straight away rather than keep giving them chances

His own mistake was taking those decisions too slowly; once someone is in the company you have far more signal than in the interview

Scope: applies to people you were confident about at interview but doubt once inside

51:50 20VC: ElevenLabs Hits $200M ARR: The Untold Story of Europe's Fastest Growing AI Startup | The Real Cost of AI from Talent to Data Centres | How US VCs are in a Different League to Europeans | The Future of Foundation Models with Mati Staniszewski

Chandra Narayanan · Mar 13, 2024

Detecting that someone isn't performing is the easy part; the hard and necessary work is diagnosing whether the cause is a skill gap, a knowledge gap, or a values/culture gap

Productivity data reveals underperformance without needing to ask around, but not all underperformers are bad — they may be in the wrong role or be deep thinkers — so you must identify the actual cause before deciding it's fixable

59:38 20Growth: Top Five Lessons from Leading Analytics at Facebook and Data Science at Sequoia Capital, The Two Skills Required to do Analytics Well, The Three Types of Execs within Companies and When and How to Hire for Growth with Chandra Narayanan

Max Levchin · Feb 5, 2025

When criticizing work you must first distinguish whether the person can do better or genuinely cannot — if they can, frame it as 'this isn't your best work but I know what you can do'; if they truly cannot, don't worry about being too direct because the next conversation is about them leaving the team

Empathy requires diagnosing whether the failure is one of circumstance and effort (fixable) or of ability (not fixable), and the feedback should differ accordingly

6:05 20VC: Affirm Max Levchin on Why Grading Talent by Letter (A or B) is Total BS | How to Create a Culture of Post Mortems and Writing | Why You Should Only Study Failure Not Success & The Biggest Surprises Scaling to $18.7BN Market Cap

Kim Graves · Jun 27, 2025

Underperforming reps should be diagnosed by working backwards through results, effort, knowledge and skills (the REKS framework) to locate the actual failure point

Pinpointing whether the gap is effort, account prioritization, discovery skill, or product/customer knowledge tells you whether the rep can be coached or whether it won't work out

Scope: framework originally learned from Winning by Design

37:14 20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves

Amjad Masad · Mar 10, 2023 · hedged

Leaders are often too hasty in letting go of people who have outgrown their role; you can frequently find another place in the org where they'd be happy and productive for a longer period

There is sometimes an intersection between where the person would be happy and productive and where the org actually needs people — and you can arrange it so the change doesn't look like an obvious demotion

Scope: only when such an intersection exists

18:04 20VC: Why AI Will Lead to Thousands of Billionaires and Elon Musk's, Will TikTok Be Banned and How Facebook Should Be Investing in AI & Why Startups Have Become Too Soft; We Need a Spiritual Reform with Amjad Masad, Founder & CEO @ Replit

Ryan Petersen · Nov 13, 2023

When you stretch someone into a role too far beyond them, they almost always leave rather than step back, and companies should instead be able to move them back into a role that matters

Egos and compensation make stepping back hard, so the company loses great talent it could have kept

Scope: Flexport hasn't figured out how to do this well

30:44 20VC: Flexport's Ryan Petersen: Reflections on Leadership from 13 Years Leading Flexport, Why Velocity not Speed is Most Important in Company Building, How Money Creates Inefficiencies in Scaling, The Future of Trade with China & Why Remote Work is so Cha

Sridhar Ramaswamy · Feb 10, 2025

Being willing to demote someone does not mean you should fire them — reshaping a job to fit the person is legitimate leadership

In fast-moving environments a scope can explode from 20 to 100 engineers through no fault of the person; they aren't bad or incapable, they were given an impossible job, and the business can't wait

16:54 20VC: Why Model Providers Will Kill Many Startups Moving into the Application Layer | Why Deepseek is not a Threat to OpenAI & Why OpenAI Beats Anthropic | Apps vs Models vs Infrastructure: Where is Value in AI with Sridhar Ramaswamy, Snowflake CEO

Mike Shebat · Nov 27, 2023

Almost every CEO, including highly successful ones, procrastinates too long on the corrective feedback conversation with an off-culture employee

Scope: including ones who have been incredibly successful

27:31 20VC: Keith Rabois and Mike Shebat on Creating an Olympian Mindset to Work Ethic, Why First-Time Founders are Better Than Serial Entrepreneurs, Why Remote Work Does Not Work, Why the Best Founders Always Start in their Teens & Why Companies are Cults?

Chandra Narayanan · Mar 13, 2024

Performance improvement plans fail because of timing, not because the tool is useless: by the time one is opened the manager has already decided there's no chance, whereas intervening when success odds are still 60-70% can work

Managers intervene about three months too late because they are conflict-averse and unwilling to have honest, direct conversations, so by the time a plan starts the probability of success is 1-10%

Scope: he would drop the 'performance plan' label and simply help the person; if you can't help them, make them see it's best for both sides

61:15 20Growth: Top Five Lessons from Leading Analytics at Facebook and Data Science at Sequoia Capital, The Two Skills Required to do Analytics Well, The Three Types of Execs within Companies and When and How to Hire for Growth with Chandra Narayanan

Sri Batchu · Jul 26, 2023

Skill gaps are easy to address through a direct conversation and a role change or exit, while motivation gaps are harder and should be solved by understanding what motivates the person before taking more drastic action

A high performing team requires understanding what drives each individual, and what drives people is usually not company profit but their own personal motivations

28:13 Distinguish skill gaps from motivation gaps since motivation requires deeper understanding

Matteo Franceschetti · Nov 20, 2023

Before exiting a low performer you owe them a frank conversation and a real chance to improve, because underperformance almost always has a cause other than the person being bad

Most people are not bad; usually it's a fit problem with the culture, the product, or the stage of their life — and their intense culture isn't right for everyone

53:39 Owe underperformer a frank conversation and real chance since cause is usually not the person

Harry Stebbings · Nov 20, 2023

Redeploying a weak executive into a different role is usually a mistake; the test is whether you would have hired them for that new role against the other candidates, ignoring the existing relationship

54:43 Redeployment test is whether youd hire them fresh for that role

Matteo Franceschetti · Nov 20, 2023

Once a manager has given an underperformer a real chance and it hasn't worked, you should pull the plug immediately rather than letting them stay three months while a replacement is found

It's disrespectful to leave someone hanging when you've already decided to replace them, and while they're still in the seat you'll never seriously find the right partner

55:04 Once decided execute termination immediately rather than let it linger

Amjad Masad · Mar 10, 2023

Acting on loyalty to early employees who are no longer working out is a bad trade-off; leaders should reframe it as harming the collective and do right by the company by layering, replacing or moving them

The loyalty instinct comes from a tribal way of living in our DNA, but in a free-market enterprise it is deleterious — you're showing empathy to one individual while harming the rest of the company, the customers and the investors, which is utilitarian-negative

16:56 Loyalty instinct is tribal and should be overridden for collective good

Guy Podjarny · May 24, 2023

When someone consistently isn't working out, letting them go serves their interests as well as the company's

Keeping someone in a failed position does them no favor; in hypergrowth a leader falling behind must become twice as good just to keep up with a company doubling in size, so you're setting them up for failure

50:00 Termination serves the underperformers own interest especially in hypergrowth

Larry Shurtz · May 10, 2024

How quickly to act on a struggling rep depends on the nature of the red flag, and as an employer you owe people candid conversations, feedback and coaching first

Hiring mistakes cost a lot of money and time, onboarding is hard, and as an employer you have a responsibility to employees; start by asking the rep how they thought it went

27:08 Action speed should match flag severity with coaching and feedback first

Larry Shurtz · May 10, 2024

In sales, preparation, diligence and interpersonal skills are non-negotiable 'mental errors', unlike skill-based 'physical errors' which can be coached

His sports coaches' rule that you can make physical errors but not mental ones transfers to sales; interpersonal issues should be sniffed out in the interview process

28:13 Mental errors like prep diligence and interpersonal skill are non negotiable unlike coachable skill errors

Chris Sacca · Oct 11, 2021

When people underperform, it is never a lack of raw talent — it is always a lack of effort and ownership

At Google the full board deck was shared with the entire company every Friday and it took four years before a leak, whereas a prior company that withheld information from staff had people who maintained confidentiality like children

33:12 Underperformance is always a lack of effort and ownership never raw talent

Mike Salguero · Apr 5, 2023

When someone underperforms, the leader must decide whether they can get there with help or whether it was simply the wrong hire, and in the latter case be open with them and part ways

6:23 Binary diagnosis coachable with help vs wrong hire then transparent parting

Mike Salguero · Apr 5, 2023

Moving an underperformer to a different department is usually a way to avoid a hard conversation, and it serves neither the leader nor the employee

Hiding the problem robs the leader of the growth that comes from having the hard conversation, and nobody wants to be the known poor performer relocated inside the org

6:40 Lateral transfer to avoid hard conversation serves neither party

Cliff Weitzman · May 9, 2026

The right intervention for an underperformer is a 72-hour ship deadline with scope cut aggressively; if they still don't ship, they are simply not an outcome owner and you must decide whether you tolerate that

Riding a feature all the way through PR review, QA and release live is what distinguishes an outcome owner from just an engineer

56:43 Forced short ship deadline with cut scope as the test

Kim Graves · Jun 27, 2025

Whether a skills mismatch is fatal should be judged by its negative consequence: a rep who closes but at too low a volume for the motion means you need a different skill set, whereas a rep bringing in 'churn bombs' means you need better qualification

The nature of the downstream damage tells you whether the fix is a different hire or a process change

39:29 Consequence type determines whether mismatch is fixable or requires different hire

Jean-Denis Greze · Jul 21, 2023

Founders should give a struggling function lead a genuine chance — but only about three months — because waiting twelve months plus a new hire's onramp wastes eighteen months of company momentum

The human thing is to not put someone in a box based on who they were when they joined; but delay compounds into lost momentum, which is dangerous

9:57 Give a genuine but short about three month chance since waiting longer compounds lost company momentum

Des Traynor · Jul 18, 2022

When you assign someone work you suspect they may not be able to deliver, you should explicitly spell out the scope, timeline, quality bar and expectation, get their verbal agreement, and require them to flag any change early

If they disagree with the framing you're simply not aligned on their capability or on what's reasonable, and shouldn't be working together; if they agree, an early flag lets you correct course quickly on important work

50:17 Explicit scope timeline and early flag agreement tests whether a person can deliver risky work

Craig Courtemanche · Dec 4, 2023

When a loyal leader puts in the inputs but isn't delivering the outputs, you must make the tough call — coach them, then try to reposition them internally, and if that fails exit them with empathy and help them find another job

You never wake up one day and discover someone isn't scaling; the warning signs accumulate beforehand, so the process can be handled in stages

44:44 Coach then reposition then exit with empathy for loyal underperforming leaders