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The magic of group coaching lies in the safety to ask

Remember when our teachers used to encourage us to ask the “dumb” questions because if we were wondering, chances are others were too? They were so right! And I’ve carried this with me as a life philosophy.

It’s also a guiding principle in our SIMPLE coaching program. Because I believe to my core that what new leaders need more than lots of content is a safe space in which to challenge that content – to be open about what holds them back from doing the thing they’re learning, and to problem-solve how to overcome those obstacles.

So today, I’m sharing some questions I’ve received in current cohorts, and some advice provided in return. Because maybe you too have one of these questions…which are so not dumb!

OK, and now. The questions posed by our bold and lovely SIMPLE participants.

Q1: I know listening, empathy, and humility are important. But also, my team needs to have confidence in me as a leader – to believe I have answers. I’m struggling to strike this balance. Any advice?

A1: The biggest mindset shift new leaders must make is recognizing their job isn’t knowing the answers, but rather cultivating them. Leadership isn’t about what you know but what you can make known – through asking great questions and creating a safe space in which lots of ideas and opinions can be contributed.

Leadership is finding the collective wisdom in the conversation and distilling it into guidance. It’s knowing your own expertise and also knowing your blind spots and being willing to let others fill in your gaps.

It takes way more confidence to say, “I’m not sure but let me find out” or even “Great question – what does the rest of the team think?” than it does to make up your best guess in the moment.

When a question is asked, do make sure it gets answered. But know that answer doesn’t have to be fabricated in your mind alone.


Q2: I ask my team for feedback regularly – on my own leadership, on a project or approach…but I don’t generally get much of a response. What am I doing wrong?

A2: I get this one a lot. And here’s the trick – you need to ask a better question, one that (lovingly) demands a response.

When we ask, “do you have any feedback for me?” we generally get a “nope.”

But when we ask, “would you please share 3 things I’m doing well and 3 things I might shift or tweak to better support you?” your team can’t help but offer you insight.

Likewise, instead of asking “What do you think of my plan/idea?” (And getting only thumbs up), try “I’d love your help in spotting any risk or blind spots – what could possibly cause this to fail and what would you recommend?”

See the difference? Give it a try. You’ll get a better output every time.


Q3: I know delegation is important. But the last few times I delegated I got burned. It wasn’t done entirely right or well. And now I’m kind of gun-shy to try again.

A3: You’re right. Delegation is important – it enables both organizational efficiency and on-the-job development. Everyone wins when it’s done well.

So now comes the tough love. Because very often when delegation does awry, the best first question to ask yourself (as the delegator) is what did I do to contribute to this not-so-hot outcome?

In my experience the answer is almost always one of the following:

  • Chose the wrong person for the task – were they really best positioned to do this well?
  • Didn’t set sufficiently clear expectations of an outcome – your vision wasn’t well-explained, and they were striving for a different finish line
  • Didn’t check-in and/or offer support along the way – delegation requires coaching and feedback along the way – not just at the end
  • Delegated too much too quickly – developmental delegation should happen in pieces – don’t drop a whole project on someone who’s only ready to do the first draft

Our SIMPLE coaching participants have expressed that the freedom to move beyond the “steps” and the “shoulds” – and to have the space to say “sure, but when it doesn’t work what can I try instead?” has been invaluable to their development.

Curious about whether your organization could benefit from the program? Please get in touch. No strings. And we promise to keep it simple 🙂