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How to Work with an Indecisive Boss

One of the biggest “Do you have a private minute?” questions we get asked by managers is “How do I get anything done with my indecisive boss?”

Okay, the conversation is actually less polite. It’s usually more along the lines of:

“Aghhhhh, Karin and David do you see what I’m talking about? Did you watch him in that meeting? He postponed EVERY SINGLE decision. He’s the most indecisive boss I’ve ever worked for.

Why can’t he make a decision? We’ve laid out all the data he asked for. And he keeps stalling! At this point I’d rather just hear a “no” than to talk about it anymore. The really frustrating thing about this decision is, there’s really not a downside here. It’s a no-brainer! What should I do? How do I help my boss get to a decision?”


We get it. Dealing with an indecisive boss is frustrating at best, particularly when you really care about your work. After all, he’s the boss, making decisions IS his job. It’s tempting to wonder why you should have to work so hard to help him.

If you’ve read Winning Well, you know what we’re going to say next. Yup, be the leader you want your boss to be.


How to Help Your Indecisive Boss Make a Decision

So here are a few ways to get your indecisive boss comfortable with making a decision.

1. Ask Strategic Questions

One of the biggest mistakes we see managers make when pushing their boss for a decision is that they do too much talking.

If you’re met with resistance, stop selling and start asking questions to understand why your boss is stuck.

  • How do you think this change would impact the customer experience?
  • Have you ever tried anything like this before? How did it go?
  • What’s driving your hesitation?
  • Who else needs to be involved in such decisions?
  • What do you think would happen if we implemented this approach?
  • What am I overlooking here?
  • What do you think your boss would be concerned about here?
  • Are there any political issues I might be overlooking?


2. Provide a Clear Path Forward

When presenting an idea to an indecisive boss, don’t just talk conceptually. Be crystal clear on what your idea would take to implement: specifically who would need to do what by when and how you will measure success.

Indecisive managers are often afraid of change because it just sounds like too much work. Show how moving forward with your plan is easier than sticking with the status quo.


3. Make it Reversible

One of the biggest reasons for decision paralysis is that it feels so permanent. Find a way to let them taste the impact of the decision in a way that can be easily reversed. Got a new process? Try it with one team. Worried about the customer experience? Try your idea out with a small subset of customers and carefully monitor the experience. It’s a lot easier to sell-in a pilot than to convince a risk-averse decision maker to make a “permanent” change.


4. Include Others

If your boss needs to socialize the idea with others, offer to tag along. Chances are if he’s afraid to make a decision, he’s equally afraid of expressing his opinion to his boss or other stakeholders.

Offer to support him with an enthusiastic, “Awesome, I’d love to join a quick call to help you socialize the idea.” Or, “What can I do to support you as you’re communicating this idea?”


5. Talk about the Pattern

If this is an ongoing problem it might be time to have a genuine conversation with your boss about why she struggles to make a decision.

It might be time for an I.N.S.P.I.R.E. conversation.

I-Initiate: I really care about the success of this project and in doing everything I can to support you and the team.

N-Notice:  I’ve noticed you are really struggling with this decision

S-Support:  For example…

P-Probe: What’s going on?

I-Invite: What can I do to make this easier?

You can download a PDF of the INSPIRE model and complete process here. 


6. Keep Trying

Keep grounded in confident humility. This isn’t about you or your boss, it’s about doing the right thing. There’s nothing more convincing than someone passionate about doing the right things for the right reasons.

Give your indecisive boss a chance to sleep on it, and try again.




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