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This article was published on March 5, 2016

5 ways great managers build amazing teams

5 ways great managers build amazing teams
Chris Paul
Story by

Chris Paul

I'm a software engineer with 17 years of experience developing a wide variety of software from web apps to open-source SDKs to embedded syst I'm a software engineer with 17 years of experience developing a wide variety of software from web apps to open-source SDKs to embedded systems for mobile devices. Right now, I manage the engineering team at HelloSign (, a Y Combinator start-up (YC11) that provides a secure, friendly, API-focused eSignature service.

What would convince you to leave for a job somewhere else?

As a manager, asking this question scared me a little. I posed it to each of the engineers on my team last month in our one-on-one’s and I worried about how they would respond. Did they feel safe enough to answer honestly or would I get fluff answers that side-stepped the question?

Imagine my surprise when I got more constructive feedback from this one question than I had in my entire first year of managing the engineering team at HelloSign, feedback about the happiness of my teammates, their thoughts on our technical direction, and ways I could improve both. Now I want to know how to keep this feedback coming.

Now I want to know how to keep this feedback coming.

Like many engineer-turned-managers, I’ve found the role to be challenging. The most difficult adjustment was learning to distribute my time and energy amongst the team on a daily basis — this, after being used to multi-hour stretches of undisturbed time, hunkered over a glowing screen with my headphones on.

After embracing the role of deflector and context-switcher, I switched focus to other challenges like finding ways to improve code quality and maintain high team morale. I want our team to be great!

team work
Recently I’ve learned that one way to achieve team success is to cultivate an atmosphere where people feel free to take risks.

Why is risk-taking important?

A survey recently published by Google reveals that the main factor contributing to team success is not education or the personalities on a team but psychological safety: Do people feel safe enough to take risks?

Risk in software development is a 4-letter word. It’s typically something to be analyzed, managed, and mitigated, not encouraged. However, Google’s survey refers to the kind of risk you take when you reveal the boundaries of your knowledge, or challenge a teammate on their design approach, or answer hard questions candidly.

When team members feel free to risk being honest without the fear of being criticized or ridiculed or punished, the best ideas win out in conversation, design reviews are faster, and your team operates more efficiently.

How do you cultivate a risk-positive environment?

I’m still figuring this out. Asking a question that scared me a little in my one-on-one’s gave me a hint, though: I can try to lead by example. After discussing with some of my team, we came up with several other ways to encourage a more open environment.

contact, team work, people

  1. Ask tough questions. Encourage honest feedback by asking questions that get to the heart of issues your team may be facing. By doing this, it demonstrates risk positivity by showing you’re open to criticism. A tool I’ve used for managing my 1-on-1’s, Lighthouse, helps me do this by providing an exhaustive and growing list of just such questions: “What is the #1 problem at our company?”, “Are you uncomfortable giving any of your peers constructive criticism?”, “What worries you?
  2. Embrace mistakes. You’re human and you’re going to make them, so embrace the opportunity for growth. You should also respond in kind when teammates make mistakes. Neal O’Mara, HelloSign’s CTO, responds to problems like a production bug by saying, “Good catch,” or “Thanks for the heads up,” followed by a suggestion to fix it or a question as to how we should proceed. There’s no finger-pointing, just open dialogue and the desire to avoid the same mistake in the future. Demonstrate that a mistake isn’t the end of the world and that the team is strong enough to handle it and learn from it.
  3. Celebrate effort, not just results. This is a common parenting tip but it’s applicable to team members of all ages. When you only toast the successes, it’s easy to cultivate a fear of failure and risk taking.
  4. Say, “I don’t know.” This is particularly difficult to do as a manager when your instinct is to project 24/7 competence, awareness, and positivity. Solicit answers publicly. Don’t bullshit. Demonstrate that not knowing is an invitation to find the best answer.
  5. Invite private criticism. At the end of one-on-one’s, HelloSign’s CEO, Joseph Walla, is known for asking: “Do you have any feedback for me?” I’m considering taking this a step further and explicitly asking, “What is something I could be doing better? What is a criticism you have for me?” This may not work until you’ve developed rapport with someone, but offering a consequence-free path for feedback demonstrates vulnerability and trust in your team’s opinions. You might also gain some valuable insight. By doing this frequently, you prime yourself and the team to respond quickly and correctly when the criticism really matters.


I realize these tips are easier said than done. Ok, they’re really hard! However, I challenge you to experiment with each. Make this a habit and I suspect your team will feel safer taking risks, risks that lead to a more efficient, confident, and relaxed team.

And finally: What do you think? Do you have any criticism for me?

This post originally appeared on HelloSign

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