Helping your boss think out loud isn't as dangerous as you think

Yesterday I was talking with one of our clients about a challenge he was having with his boss.


This particular boss is simply amazing at coming up with new ideas and bringing them to the team for implementation. While most of these ideas are great, the team has a hard time implementing change with their current pace and schedule, so my client has been taking it upon himself to ask some questions of the boss to understand and flesh out the idea before getting the rest of the team involved.

You may see what's coming.

When my client begins asking, "Hang on a second - why would we do that? I mean, what do you hope to achieve by that change?" the boss doesn't see the question as helpful.  He sees it as a threat to his efforts to make the company better. The conversation tends to go a bit downhill after that, with both my client and his boss trying not to be defensive, but both doing it anyway.

Here's another counter-intuitive option that I've found works amazingly well.

Just go with it

What I mean is, instead of backing up and saying "Whoa!" to new ideas you don't understand or believe may have some serious holes, walk the person forward to the future. Give them permission to have their idea be successful.

This looks something like "Hmmm. Ok, let's say your idea is fully implemented and successful. What does the organization / team / my job look like?"

Bringing the future to the present allows them to explore their own thinking and allows you to gain more understanding and ability to influence the exploration. Once you give them permission to have their idea be successful, questions like, "So then how do you think Sue's department / our client / my job would benefit from the change as a result?" are much more likely to be seen as collaborative help.

It may feel risky to encourage your boss to do even more thinking when you're already feeling whipsawed by the intensity and seeming randomness of his or her ideas. Yet if you are willing to step into the danger and endorse your boss' idea first before exploring it, your boss is more likely to see you as a thinking partner and not someone who gets in the way of her or his desire to make the company better.

Chris Hutchinson, CEO

Chris Hutchinson, CEO

(After all, if you take an idea to your boss, you'd rather have your idea be considered worthy and get your boss' help figuring out how to make it really successful instead of geting a bunch of objections to it, right? Hint: your boss is the same.)


Chris Hutchinson

As CEO of Trebuchet Group, Chris Hutchinson thrives working with clients and his team to improve organizational clarity, teamwork, and leadership impact.

After years of building Legos® and tree houses around the world, Chris earned his Mechanical Engineering degree and followed that with an MBA. His experiences in the military and the business world taught him great leadership can be learned, and everyone is in some way a leader.

Clients and peers describe him as an inspirational catalyst for positive change. He is the author of Ripple - A Field Manual for Leadership That Works.

Chris and his wife live, garden, and bike in Fort Collins, Colorado, and have four children. He has an unrequited love affair with brownies.