Management Debt Series: Learn How To Deliver Feedback

Management Debt Series: Learn How To Deliver Feedback blog post.

It’s been said time and again that people don’t quit jobs; they quit managers. And why do they quit those managers? Because those managers often don’t know how to manage. And one of the most common symptoms of this affliction? The poor, ineffective, muddled, and occasionally offensive delivery of feedback. Let’s embark on another Management Debt Series lesson focusing on this often misunderstood art.

What is feedback?

Feedback, at its core, is a communication process where one provides insights, evaluations, or suggestions to another, ostensibly with improvement as the objective. It’s more than just praise or criticism; it’s an essential tool for personal and professional growth.

Why does it matter?

Startups have to get better or perish. And startups are simply collections of humans. That means the humans have to get better or, collectively, they will (economically) perish. And feedback is the mechanism for improvement.

Management Debt Series: Learn How To Deliver Feedback blog post.

Let’s start with some basics.

You have something to share with a team member. They did something poorly, and a learning opportunity has surfaced. Where to start?

  • Safety first. Presuming your employee doesn’t have a glass jaw, then first up is to make sure you’re in a relaxed, calm mental place. Your energy will impact their energy. If they feel safe, they’ll hear you. If they’re afraid, they won’t.
  • Ask permission. “May I give you some feedback?” Asking permission is one of the simplest hacks in life to reduce defensiveness. It reminds the recipient of your feedback that they matter and that they have agency despite the employer-employee relationship. 
  • Employ radical candor (thank you Kim Scott). Ambiguity helps no one. Ensure your feedback is kind, precise, and actionable. 
  • Behaviors over personality. The person is not the problem. The behaviors are what require feedback. In your language, focus on the latter.
  • Call out counterexamples. If you’re not firing the person, I’m guessing there are ample examples of the team member getting the job done right. Don’t forget about those. Reference them. Offer a balanced view of positives alongside the constructive points.
  • Use “we” not “you”. No one wants to feel isolated, or separate from the team. The more you can position feedback as a collective observation or opportunity rather than personal criticism, the more the employee will sense your investment in their future.
  • Get to agreements. Telepathy is not a thing. Ensure both parties understand and commit to actions. Codify it. Explicitly agree. No guesswork or assumptions. 
  • It’s a gift. Well-intentioned feedback has but one purpose – growth. Employees want to get better. They want to improve. You are giving them a chance to do that. In other words, you’re giving them a gift. Remember that.

And if basics are not good enough? How do the best managers practice feedback?

  • Public vs. Private. Celebrate achievements publicly, but always provide critiques in private. For most employees, public critique is akin to an attack, and relationships rarely survive such attacks. 
  • Set and Setting. The more sensitive the feedback, the more personal the method. The most difficult topics? Meet in person. Have something minor to share – a text might suffice.
  • Communication. The best managers know that the key to feedback is safety. And that safety requires two recurring forms of communication — relational and transactional. The former builds trust. The latter gets shit done. Too much of either and the relationship breaks. 
  • Curiosity. No matter how triggered, or inflamed, the best managers stay inquisitive rather than inquisitional.
  • Charitability. The best managers practice what we call generous listening (h/t Steve Chandler). They listen fully, without distractions, always assuming positive intent.
Management Debt Series: Learn How To Deliver Feedback blog post.

Common questions we receive about feedback.

1. I have an employee who once was wonderful and now is not. How should I handle it?

We recommend reading this story about Randall. Share with that employee the times you’ve loved working with them — and the times you have not. Then ask what support you can provide so you can experience far more of the former and no more of the latter.

2. I have an employee who is great functionally but a poor fit culturally. What would you do in this situation?

We’re strong believers that, over time, the best cultures win. The healthier the culture, the more the team members trust one another. Trust accelerates learning, and the velocity of learning is what distinguishes successful startups from their failed counterparts. So, if someone’s behavior is not consistent with your aspirational culture, move swiftly to correct it. Protect your culture, and then decide if you’re all-in or all-out

3. Should I document all the feedback I deliver to my people? HR told me I should …

We have a contrarian view here. Only document feedback for two reasons: 1) to facilitate clear agreements with an employee or 2) if you’ve already decided to fire someone. Most HR professionals reasonably consider legal risk mitigation to be their primary role. But most U.S. employees are savvy — they don’t see written feedback as a tool for improving performance or building trust; they see it as the precursor to termination. And that means the moment they read formal HR language, they will begin looking for new employment. If that is what you want, then, by all means, document away. But if what you really want is to develop a team member, then shy away from HR formalities. Just talk to your employee like a person who’s trying to get better at their job. 

4. Our startup is still young — in fact, we have fewer than 50 people. Should I have a formal performance review process already? It feels too corporate for us. 

Employee happiness can be reduced to two simple things: safety and progress. Achieving the latter means an employee knows the definition of success and where they stand along the way. It doesn’t have to be heavy with 360 reviews and quantitative surveys, but even for the youngest of companies, having a structure by which to set agreements, measure results, and provide feedback is a must-have for long-term employee satisfaction. 

5. The feedback I have is so harsh, that I’m struggling with finding the right words. What should I do?

First, start with the unadulterated truth. Imagine your employee could hear you with zero emotional noise. Zero defensiveness. What would you say? Write that down. Second, round out the rough edges. Play with various ways to soften the most jarring language. To seek inspiration, drop the text into ChatGPT with a prompt “Soften the language without losing any of the meaning.” Third, practice the language with a neutral 3rd party until you’ve found the balance of clarity and kindness. Repetition eliminates fear; so when the stakes are high, practice.

6. Do you hold meetings that are more specifically designed as feedback sessions? 

Feedback of some sort shows up in every type of work-related human gathering. However there are a few specific types of meetings where feedback is the purpose.

Here are a few:

  • Retrospectives. Regular reflections on completed projects or periods. When done well, they cover: 1) What was the mandate? 2) What actions did we take? 3) What results were seen? 4) What did we learn? Retros are efficient and blameless structures by which a company can get smarter. 
  • One-on-Ones. Want to make one change to improve how feedback is gathered at your company? Ritualize one-on-ones – not just the delivery of them, but the quality of the delivery. 
  • Performance Reviews. Formal evaluations commending an employee’s overall contributions, providing feedback, and collaborating on what future success would involve.
Management Debt Series: Learn How To Deliver Feedback blog post.


Many of us have had a wonderful manager at some point in our careers. The person who listens, who cares, who makes a great effort to improve the lives and skills of those in their charge. The first step to being a great manager is having the desire to be a great manager, and great managers are great at delivering feedback. By handling feedback with clarity and compassion, a startup not only retains talent but also cultivates an environment where everyone might Enjoy The Work just a little bit more.

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