How to Encourage More Assertiveness from Your Team

Written by Dave Bailey

Team speaking up to each other

As leaders, we all need team members who are assertive. If your team isn't speaking up, learn how to encourage more input and feedback that's constructive and effective.

Simple advice to get the most out of assertive and non-assertive team members.

Many founders score highly on assertiveness. It’s one of the things that make entrepreneurs exciting to be around. Their confidence is so inspiring that we find ourselves asking, ‘What if they’re right?’

When I took the Myers-Briggs assessment about 10 years ago, I came out with an ENTP-A. The ‘A’ at the end stands for Assertive: the tendency to actively defend, speak up for, and act in the interest of your own goals. I came out particularly high on assertiveness, scoring 83%.

This personality trait has helped me get each of my businesses off the ground. Like most entrepreneurs, I love the challenge of convincing investors to put money in, attracting talented people to join me, and winning over my first customers. Assertiveness has its benefits.

However, you can have too much of a good thing.

The Dark Side of Assertiveness

The ability to defend your ideas is very useful . . . when your ideas are right. The problem in business is that none of us knows for sure whether we’re right or not. This is why an open mind, and the challenging of ideas, is essential, especially if you’re building something new.

When you present your ideas assertively, it’s not always clear that you want to be challenged or that you’re open to new ideas.

Assertiveness can come off as defensiveness, and if you stray into defensiveness — even if you are genuinely open-minded — you can find yourself surrounded by silence.

Once your team starts holding back their thoughts, your assertive-self will fill the space with more ideas. Soon, your ideas become instructions. And finally, the inevitable happens — one of your ideas turns out to be completely wrong.

‘We tried to tell you,’ the team says, with a pinch of resentment.

‘I was just making suggestions,’ you reply — not realising that an assertively-said suggestion sounds like a command. ‘These results are your responsibility.’

You walk away wondering why your team isn’t speaking up. But before you conclude that you hired the wrong people, take a look in the mirror. They might think the problem lies with you.

The Assertive Sweet Spot

Researchers at Columbia University quantified the problem of too much assertiveness years ago. In their paper, ‘What Breaks a Leader: The Curvilinear Relation Between Assertiveness and Leadership’, Daniel Ames and Francis Flynn found that increased assertiveness correlates with increased short-term achievement . . . but it comes with a social cost. If you’re too assertive, you become ‘socially-insufferable’.


Every strength has its weakness. And when it comes to assertiveness, you need to find the sweet spot.

How to Get Your Team to Speak Up

In The Five Keys to a Successful Google TeamJulia Rozovsky describes how psychological safety — when team members feel safe to take risks and be vulnerable — is positively related not only to harnessing ideas, but also to increasing revenue.

If you want to encourage your team to come up with their own ideas and debate them openly, the more assertive members need to curb their defensive tendencies.

Which camp do you fall into? Are you more assertive or less assertive? Here are some pointers for both groups, to help rebalance the conversation and uncover better ideas.

For the Highly-Assertive:

1) Adopt the question reflex. When you feel someone is wrong or doesn’t understand, get curious and start by asking questions. Think of this as ‘assertive listening’, where you commit to hearing what others have to say.

2) Aim for balance. If you’re committed to debating ideas, you need to let everyone speak. Pay attention to who is hogging the conversation and try to involve the people who haven’t spoken up. Round robins — going around the room one-by-one — are a surprisingly effective way to ensure everyone has a fair chance to contribute.

3) Avoid generalisation. I’ve noticed that assertive people tend to make more generalisations than less assertive people. However, it’s hard to argue with a generalisation. If you catch yourself making a sweeping statement, pause and think. How can you get back to the specific issue?

For the Less-Assertive:

1) Over-prepare. I’m not a natural public speaker, but practising a speech really helps me build confidence. Ask yourself, ‘How can I best communicate my point of view?’ Can you collect data or undertake some research? In most cases, power tends to gravitate to the best-informed.

2) Learn some facilitation techniques. Professional facilitators are adept at managing unbalanced conversations. Here are some useful phrases to help you chime in:

  • I think I hear you saying . . .
  • I can see this is important to you . . .
  • We haven’t heard from Lucy yet . . .
  • So far, we’ve agreed . . .
  • This is a good discussion, but . . .

3) Be vulnerable. In an environment that’s hostile to ideas and opinions, emotions can be powerful — after all, your feelings are very hard to argue with. A vulnerable statement like, ‘I’m feeling anxious because X’, or, ‘I’m scared that Y’ can have a dramatic effect on the conversation.

Strong Opinions Weakly Held

Paul Saffo came up with the phrase ‘strong opinions weakly held’ to underline the importance of proving your own ideas wrong in pursuit of the truth. While many of us agree with the concept, the ‘weakly held’ part usually isn’t obvious to other people.

If you lead people and self-identify as assertive, you may not be aware of how others perceive you. To find out, ask some questions, such as, on a scale of 0 to 10:

  • How easy am I to argue with?
  • How open am I to other people’s ideas?
  • How good am I at listening to your ideas?

Treat any score of less than a 10 out of 10 as a signal that there’s significant room to listen more and tone down your assertiveness. When it comes to asserting your ideas, choose your battles wisely. Your desire to win the next debate may cost you the truth.

Continue reading about speaking up:

Originally published Apr 15, 2019, last updated Aug 20, 2021

coaching culture founders psychology

About Dave Bailey

Hi, I’m Dave Bailey and I coach tech CEOs from Series A to pre-IPO. Join 20,000 entrepreneurs who receive my new essay every week. 

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