How frequently and in what form should managers deliver feedback?

Linda Lian · Apr 1, 2021

Transparency/directness and compassion are not opposites but two parts of the same whole — one of the most compassionate things you can do is speak the truth transparently, even when it means letting someone go.

Speaking directly is the 'what' and being compassionate is the 'how'; withholding the truth doesn't serve the person.

Scope: in practice the two can still be at odds; she admits failing on the compassion side herself

13:15 20VC: How To Deliver Feedback with Compassion and Clarity, WTF Are Values Really and How To Instill Them & Raising $50M+ From Index and Greylock but Remaining in Stealth for 12 Months with Linda Lian, Co-Founder & CEO @ CommonRoom

Linda Lian · Apr 1, 2021

The 'shit sandwich' (praise, criticism, praise) is a bad way to give feedback; feedback should be given directly, transparently and honestly instead.

Direct feedback is a more efficient way of communicating and isn't antithetical to compassion; wins and mistakes get celebrated as a team.

Scope: she says she is still working on feedback delivery herself

15:12 20VC: How To Deliver Feedback with Compassion and Clarity, WTF Are Values Really and How To Instill Them & Raising $50M+ From Index and Greylock but Remaining in Stealth for 12 Months with Linda Lian, Co-Founder & CEO @ CommonRoom

Jeff Jordan · Jan 16, 2023

Hard conversations are in the other party's interest, and adopting that lens makes them much easier to have

If you want someone to succeed in the organisation you owe them the tough conversation; seeing it as being charitable rather than critical removes the difficulty

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David Schneider · Sep 11, 2024

Immediate, blunt feedback from a leader is a culture-building act and earns respect rather than resentment

In hindsight he understood where Slootman was coming from and respected him for coming straight to him; the moment became his defining lesson in how culture is built and destroyed

59:09 20VC: Scaling ServiceNow to $5BN in ARR | Leadership Lessons from Doug Leone, Frank Slootman and Bill McDermott | VC Value Add: Is it Real and Why the Worst VCs are "Seagull VCs"

Alan Chang · Jan 5, 2026

Leaders should build a truth-seeking culture and voice ugly truths even when they hurt someone's feelings

Saying it makes that person better

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Harry Stebbings · Mar 9, 2020

The speaker and their partner practice immediate radical transparency so that issues are never left hanging

Scope: stated as the thesis he and his partner adopt, before asking Mochary whether timing changes it

14:44 20VC: Matt Mochary, Coach To Silicon Valley's Leading VCs & Founders on How To Deal with Imposter Syndrome and Self-Doubt, How To Manage Fear and Anger & Why Board Seats Are The Death of Investors

Harry Stebbings · Aug 17, 2022

Tough conversations from day one engender greater trust, because unstated doubts are what breed insecurity in employees

Knowing where your manager doubts you is fine; not knowing where or why is what creates insecurity

37:01 20 Sales: Three Reasons Why Sales People Fail | The Two Things That Matter When Hiring Sales Leaders | Why Revenue, Discounting and Price Do Not Matter in the Early Days with Jordan Van Horn, Revenue Leader @ Monte Carlo

David Schneider · Sep 11, 2024

Feedback is a gift and should be delivered frequently and as close in time to the situation as possible

He has received such feedback himself and made massive corrections to his behavior as a result

56:53 20VC: Scaling ServiceNow to $5BN in ARR | Leadership Lessons from Doug Leone, Frank Slootman and Bill McDermott | VC Value Add: Is it Real and Why the Worst VCs are "Seagull VCs"

Paul Erlanger · Jun 27, 2026

The single most valuable thing a founder can do is have hard conversations sooner

Hard conversations with employees, early investors and friends are the hardest part of being CEO and people avoid confrontation, but if you're transparent and come from the best place, people understand

48:27 20VC: How We Got Fred Wilson, Benchmark and Index to Invest $94M | Why Robinhood's Strategy is Wrong | Why 1-1s are BS and What Every Founder Gets Wrong About Equity | Why Taste Beats AI But How AI Kills Org Charts with Paul Erlanger, CEO @ fomo

Harry Stebbings · Jun 27, 2026

Hard conversations are usually less bad than anticipated, and completing one creates a domino effect where you take on more hard things

The sense of accomplishment from finding it easier than feared makes you willing to attempt the next difficult thing

48:54 20VC: How We Got Fred Wilson, Benchmark and Index to Invest $94M | Why Robinhood's Strategy is Wrong | Why 1-1s are BS and What Every Founder Gets Wrong About Equity | Why Taste Beats AI But How AI Kills Org Charts with Paul Erlanger, CEO @ fomo

Chad Peets · Jan 9, 2026

A blunt public wake-up call to an entire sales organization — telling underperformers to step up or self-select out — is an effective intervention for a company that has gone soft

Half the room thanked him and said they'd lost their way and needed the shot in the arm, even though the other half filed HR complaints

Scope: based on his August speech at Snowflake

45:51 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets

Harry Stebbings · Jan 9, 2026

Critical feedback should often be given in public because the lessons are transferable and the whole team learns from them

In a pipe review, correcting one rep on multithreading teaches everyone else; sales is an apprenticeship business, so protecting one person's feelings sacrifices the learning of everyone else

47:35 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets

Carles Reina · Feb 14, 2026

Sales leaders should run deep monthly pipeline reviews and deliver blunt criticism in front of the whole team, including telling reps they only hit numbers by luck

You need that honesty with your team; building a generational company means you can't do things the traditional way, and most reps improve the following month

25:11 20Sales: Inside ElevenLabs $330M ARR Sales Machine | The 20x Sales Comp Plan Reps Must Hit | How to Land and Expand in a World of AI | Why Product-Market-Fit is BS, Reps Should Not Be in the Office and Outbound is King with Carles Reina

Carles Reina · Feb 14, 2026

Reps should be criticized publicly, not privately — the 'praise in public, criticize in private' maxim is wrong

You can't do it one-by-one at scale, the public pressure and the learning benefit others, and if someone hasn't done their job everyone should know they're getting shit for it

Scope: not to the point of telling someone they're about to be fired

29:22 20Sales: Inside ElevenLabs $330M ARR Sales Machine | The 20x Sales Comp Plan Reps Must Hit | How to Land and Expand in a World of AI | Why Product-Market-Fit is BS, Reps Should Not Be in the Office and Outbound is King with Carles Reina

Alan Chang · Jan 5, 2026

He is untroubled by people thinking he is too harsh or too direct

35:32 20VC: $0-$260M in Revenue in Three Years: How We Did It | You Need to Work Weekends to Win — Most Founders Aren't Ambitious Enough | The Revolut Playbook: Speed, Urgency, Extreme Ownership, and Zero Excuses with Alan Chang @ Fuse Energy

Adam Foroughi · Apr 27, 2026

Being too kind rather than direct wastes time; it is better to be aggressive and rub some people the wrong way than to be surrounded by people whose concern for kindness slows the company down.

Time is limited and the loss from sugarcoating things can't be quantified, so he'd rather surround himself with people who want to push hard.

Scope: he acknowledges aggression rubs people the wrong way and that half the people who know him would call him an asshole; kindness is not a word pushed around at the company; the culture is aggressive, almost cutthroat

75:05 20VC: Applovin: $160BN Market Cap, $5.48BN Revenue, $10M EBITDA Per Head | Why the Best Do Not Need Mentorship | Why Founders Should Not Angel Invest | Why Kindness in Business Will Slow You Down with Adam Foroughi

Adam Foroughi · Apr 27, 2026

He doesn't regret rubbing people the wrong way — living in fear of that would slow your pace, so it's better to move fast and accept the risk.

He makes many decisions, a lot end up wrong, and he optimizes forward with short-term memory; when moving fast you will inevitably miscommunicate and offend people.

Scope: he still wants a long-term core group of family, friends and colleagues around him

76:24 20VC: Applovin: $160BN Market Cap, $5.48BN Revenue, $10M EBITDA Per Head | Why the Best Do Not Need Mentorship | Why Founders Should Not Angel Invest | Why Kindness in Business Will Slow You Down with Adam Foroughi

Matt Mochary · Mar 9, 2020

The timing of a difficult conversation must be agreed upon by both parties rather than delivered immediately; forcing it on someone will not produce a good result

You cannot impose it on someone who is stressed about another situation or mid-task; asking 'is now an okay time?' lets them name a time that works

15:11 20VC: Matt Mochary, Coach To Silicon Valley's Leading VCs & Founders on How To Deal with Imposter Syndrome and Self-Doubt, How To Manage Fear and Anger & Why Board Seats Are The Death of Investors

Harry Stebbings · Dec 11, 2023

You should not always raise an issue immediately — it is important to pick your moment for a difficult conversation

Sometimes you're exhausted, your child hasn't slept and you're not in the right state; other times you're calm and can have a quiet, thoughtful discussion

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Harry Stebbings · Feb 19, 2024

The advice to address problems immediately with radical candor is bad advice — it is never a good idea to have the confrontation in the moment

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Lauren Schwartz · Oct 19, 2022

Her world-class strength as a sales leader is transparency and direct communication that creates a culture where people feel safe talking about mistakes

It matters to her that people own their learnings and share them with the rest of the team

33:30 20 Sales: How To Structure The Interview Process for All Sales Reps, The Must-Ask Questions When Identifying Potential Sales Talent & The 3 Biggest Mistakes Founders Make When Hiring Their First Reps with Lauren Schwartz, VP of Enterprise Sales @ Fivetran

Micha Kaufman · Jun 9, 2025

Home should be an unconditionally safe place — you can be candid and even judgmental, but never to the point of breaking the person, because the motivation must be to help them; the same principle should carry into management style

The purpose of candor is help, not damage, so support must be unconditional whatever the person has done

Scope: applies to both parenting and leadership; doesn't mean withholding judgment entirely

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Matt Mochary · Mar 9, 2020

Difficult feedback should be framed entirely in terms of the speaker's own feeling, own thought, and own request rather than as an accusation about what the other person did

Pointing a finger and saying 'you did this, you shouldn't have' makes people defensive; centering it on your feeling, thought and request assigns no fault or blame, so the receiver can actually hear it and act on it if they choose

Scope: he credits existing literature rather than inventing this

13:22 20VC: Matt Mochary, Coach To Silicon Valley's Leading VCs & Founders on How To Deal with Imposter Syndrome and Self-Doubt, How To Manage Fear and Anger & Why Board Seats Are The Death of Investors

Chris Sacca · Oct 11, 2021

The effective way to give critical feedback is to state your own feelings and then ask the person what they think should be done, so they own the solution — jumping straight to prescribing the fix is the least effective way to manage

People crave being heard and validated before problem-solving; letting them find the solution themselves means they own it, whereas imposing it produces defensiveness and doesn't prevent recurrence

Scope: frame the failure as 'we' rather than assigning blame, even when one person clearly erred

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Chris Degnan · Nov 10, 2023

In the corporate world nobody is really your friend — you have a job to do and an obligation to shareholders — and operating on that premise is how tough feedback should be given, without being mean.

Frank pointed out the board would fire him in a heartbeat if he weren't performing, and Chris saw the Snowflake board fire Bob Muglia, who thought they were his friends.

Scope: you don't have to be an asshole about it

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Chad Peets · Jan 9, 2026

A blowout argument with Sigma CEO Mike Palmer was followed by five years without another argument, because both sides now give each other direct feedback and recognize they want the same thing: the objective and the mission rather than either person's feelings

He and Mike Palmer had a screaming argument five years ago, said everything they had to say, and have not argued since — both wanted things done correctly and to drive company value

Scope: based on his relationship with one CEO

6:29 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets

Max Levchin · Feb 5, 2025

Being opinionated is exceptionally valuable in a teammate, and the pinnacle of teamwork is voicing harsh opinions without offending the person so badly they opt out

If you don't deliver the blow and tell the team what they built is terrible, you will ship garbage; the skill is couching the blow while still giving it

5:15 Opinionated harsh feedback is valuable if delivered without driving people to opt out

Alan Chang · Jan 5, 2026

Shielding your best performers from harsh feedback isn't protecting them, it's hiding information from them

Top performers are smart and hardworking, not dumb; they internalise negative feedback well and find ways to improve — he resisted Nik's feedback at first but it made him better

36:00 Top performers need the harshest feedback not protection

John McMahon · Nov 28, 2025

Being blunt and hard as a leader is fine as long as you also have the art of the sale — reading who is in front of you and coaching them at their own level and pace

He can reach people at their level and pace, so once they hear him he can still coach, mentor and grow them

37:37 Bluntness works if you read and pace the person

John McMahon · Nov 28, 2025

Brian Halligan's style extracts more information from people than Dave Acharya's, because Dave's intimidating presence makes some people withhold information a CEO needs

People who are intimidated hold back and are a little afraid, so they don't give the CEO the information he should get

63:50 Approachability extracts more information than intimidation

Chad Peets · Aug 23, 2024

Delivering hard messages in a kinder, more diplomatic way is more effective long-term than his own habit of just saying what needs saying

Mike pointed out that his focus on saving time and being direct sacrifices long-term effectiveness

40:42 Diplomatic delivery beats blunt directness

Adam Mosseri · Jul 24, 2023

Blunt, uncaring criticism early in a job can be the most valuable thing someone does for you, because it lands harder in your first months than it would later

He believed he was focused and crushing it, but was spread too thin; the timing, while he was still trying to establish himself, made the feedback hit home and shaped him over the long run

62:53 Blunt early job feedback lands hardest and shapes long term development

Stephane Kurgan · Jul 28, 2023

Praise should be spontaneous and systematic but kept sparse so it retains value, while challenging feedback requires picking your moment and framing it lightly with a concrete example

Everybody knows if you are sparse with praise, so when they receive it they value it immensely

20:04 Sparse spontaneous praise retains value while challenging feedback needs careful timing and a concrete example

Stephane Kurgan · Jul 28, 2023

Feedback given without a specific example and a concrete way to improve is useless and actively toxic

Without the example and the alternative, the recipient cannot action the feedback, which creates a negative loop

22:26 Feedback without a concrete example and improvement path is toxic

Matteo Franceschetti · Nov 20, 2023

People should always know what their manager thinks of their performance; if a direct report doesn't know whether they're rated incredibly good, good or meh, the executive is doing a poor job

It prevents future problems and gives the person the opportunity to course correct

71:30 Employees should always know where they stand at minimum monthly

Matteo Franceschetti · Nov 20, 2023

Leaders should tell people upfront that they will be very direct and give feedback in real time, while inviting them to push back with a case

He doesn't claim to always be right, so people need to know how he operates and that they can build a counter-case

73:25 Set explicit expectation of directness upfront while inviting pushback

Matteo Franceschetti · Nov 20, 2023

A leader should exercise some self-control when told they're too much, but should not compromise velocity or feedback

If people understand you always have the best intention and see the point, it becomes much easier for them to accept it, and feedback is in everyone's best interest

74:11 Leader should self moderate tone but never compromise directness or velocity

Frank Fillmann · Mar 22, 2023

Formal sales feedback processes — recording and dissecting calls, or quarterly reviews — are less effective than immediate joint prep, role play and debrief where the leader asks for criticism first

Delayed formal critique never lands well and triggers defensiveness; asking to be critiqued yourself preserves safety and gets better output

19:02 Immediate joint prep and debrief beats formal delayed critique

Chris Degnan · May 23, 2026

One-on-ones must happen weekly and consistently, and must consist of hard accountability questions about the person's business rather than casual check-ins

Inconsistent cadence teaches reps they won't be asked tough questions; the one-on-one is the mechanism for holding ICs, frontline and second line managers accountable

22:29 Weekly one on ones with hard accountability questions

Jordan Van Horn · Aug 17, 2022

Blunt critical feedback delivered with a commitment to fix it is the most powerful lever for changing a manager's behaviour fast

Jenny told him five days in that he had a low hiring bar and bad judgment but that it was fixable, which changed his trajectory at Segment quickly

37:17 Blunt feedback paired with explicit fixability commitment drives fast behavior change

Jordan Van Horn · Aug 17, 2022

People don't primarily need a cheerleader; they need a clear definition of what great looks like and honest feedback on their progress toward it

He used to assume people knew what support they needed and just wanted encouragement; clarity plus progress feedback is how you both care for people and stay objective

38:00 Employees need clarity on what great looks like and honest progress feedback not cheerleading

Kevin Egan · Jul 12, 2023

Direct feedback should be a discrete moment in the manager-employee relationship rather than a constant daily feedback loop, after which the relationship returns to a congenial working mode

Feedback is a portion of the relationship, not the whole of it; people sit up straighter, dust themselves off, and then you go back to enjoying the work together

24:12 Discrete feedback moments not constant loop

Kevin Egan · Jul 12, 2023

The main feedback mistakes are getting frequency wrong (too overbearing/diminishing) and making it personal rather than tying it to team priorities

Framed via Liz Wiseman's Multipliers: feedback should be geared to the priorities the team is trying to get after, not diminishing

25:00 Tie feedback to team priorities not the person

Daniel Dines · Dec 18, 2024

His very direct, sometimes rude-seeming style is a sign of appreciation; when he starts hedging and finding his words around someone, that's the bad sign

The indirect mode is when he is avoiding telling someone what's actually wrong

41:29 Directness signals appreciation hedging signals the real problem

Harry Stebbings · Apr 1, 2021

Whether feedback lands as compassionate depends partly on the composition of the team and the types of people you hire, not just on delivery.

Compassion is interpreted through how the recipient ingests the feedback.

15:52 How feedback lands depends on who you hired

Matt Pohlson · Jun 6, 2025

The hardest thing in leadership is calibrating the right amount of feedback and bar-raising, because there's no right or wrong way and it's a constant adjustment

He could give feedback to every person every day but that would be overkill; you have to raise the bar while recognising when people are maxed out

65:21 Calibrating feedback frequency and bar raising per person is inherently uncertain and constantly adjusted

Cliff Obrecht · Jan 27, 2023

Frank, transparent feedback and coaching beats simply holding high expectations and being frustrated when people fall short

He used to assume things were common sense and get annoyed; he realized people often just don't know, and telling them directly actually helps them

11:03 Explicit coaching beats silent frustration at unmet expectations

David Schneider · Sep 11, 2024

Conflict and escalation should be handled in person, not by email — even if it means flying across the world for the conversation

His flaming escalation email at Data Domain broke trust with engineers who had built the product for three years, whereas going to them in person and asking for help got the product working in three days and produced the company's biggest deal

57:11 Handle conflict and escalation in person never by email

Des Traynor · Jul 18, 2022

The right way to deliver blunt criticism is to first get the person to buy into your general principles and then show how their idea violates them, aiming for either agreement or firm pushback

Both outcomes are good — they either correct the idea or stand up to you and go do their own thing; anything in the middle is a bad result

42:12 Anchor criticism in shared principles first then show violation to produce agreement or pushback

Hugo Barra · Nov 9, 2022

Leaders should hold hard conversations and deliver strong feedback in private and never call someone out publicly, because public humiliation degrades a person's dignity

The Chinese concept of 'face' works like a social bank account; causing someone to lose face is deeply damaging, so difficult feedback belongs in private and people should be given an out

16:39 Private delivery preserves dignity and face never call out publicly

Chad Peets · Jan 9, 2026

What matters is not whether feedback is public but the way in which it is delivered

48:17 Delivery manner matters more than whether feedback is public

Danny Rimer · Jun 17, 2024

'Compassionate' is the better frame than 'empathetic' for giving founders hard feedback

Index's own self-description is 'compassionate ass kickers', a framing he credits to Jeff Weiner

52:57 Compassionate framing not empathetic is the right lens for hard feedback

Danny Rimer · Jun 17, 2024

Good investor feedback requires being transparent and vulnerable, actively soliciting feedback on your own performance, and not holding back on patterns you have seen repeat

Being an 'ass kicker' means making sure execution happens, and founders need to hear the patterns you recognise from prior experience

53:19 Investor feedback requires vulnerability self disclosure and unfiltered pattern sharing

Matt Mochary · Mar 9, 2020

People working together should say aloud their most negative thoughts about each other, because withheld negative thoughts turn into resentment

If negative thoughts are withheld, people simply resent each other; the recipient is usually appreciative because they can only act on information they actually receive, otherwise they walk blind, upsetting people without knowing it or how to fix it

12:15 Voice the harshest unsaid thoughts to prevent resentment

Matt Mochary · Mar 9, 2020

When someone is triggered into anger, naming their feeling and voicing their unspoken thoughts back to them — deliberately overshooting how harsh those thoughts are — lets them release the anger

Overshooting makes it okay for them to have thoughts that are milder than what was said, gets it into the open, and when people feel heard for both feelings and thoughts they can relax and let go

15:58 Mirror and overshoot their unspoken thoughts

Sridhar Ramaswamy · Feb 10, 2025

The effective way to run a hard conversation is a combination of respect, straightforwardness and painful humility — openly naming that it's awkward and that you don't have all the answers

That combination goes a long way in getting the message across without demeaning the person

15:22 Combine respect directness and humility to deliver hard feedback