Successfully Disagreeing with The Boss

Leaders frequently say they don’t want “yes men”, or perhaps more properly said today “yes people.” Regardless of the pronoun, you know the idea. Not wanting leaders who just say yes or do what you say without sharing dissenting opinions or opposition to your ideas.

While it's often said, I think most leaders aren’t being truthful when they say they don’t want yes people. At least not being truthful based on the frequency of negative reactions I see to resistance, disagreement, and difference of opinion. From what I can tell, most leaders really do want yes people. It makes life easier. Things roll faster. And if you have a gazillion priorities to address who wouldn’t prefer a simpler, more accommodating approach in those we work with. This is true of all of us to a degree.

So how do you deal with your boss, whether they are a VP or Chair of the Board, when you don’t agree with their perspective or direction?

One of my rules of communication (someday I’ll publish them) is that you can disagree, without being disagreeable. Try this approach:

1. Request a short time to discuss the circumstance. This gives you the chance to have dedicated time from 10 minutes or longer to address a single topic. Always easier to keep the focus narrow.
2. Reassure the boss that when the conversation is done, you will support whatever direction they choose, policy they want to implement, approach they want you take. This takes the pressure off them worrying that they must figure out how to get you to do what they want while you are talking. Consider reading that last sentence one more time as it may be the most important here. Doing this creates receptivity to your idea.
3. Remind them that this is what they ask for. You may say, “I know you don’t want blind agreement or yes people” or “I don’t feel I’d be doing my job if I didn’t point out _________ .”
4. Share your perspective succinctly. Make your point clearly and crisply then stop.
5. Check in. You can ask “what do you think of my take on this?” or something like that.
6. Recap your willingness to support and align with the bosses direction, regardless of whether your input changed their mind.

The last step is critical here. And maybe the hardest. But your goal is to be heard, and share your opinion, direction, or take on a situation. Doing so persuasively is all you can do. You can’t control how they respond. But taking this approach gives you your best chance to be heard by a leader that really may prefer not to hear (despite saying they don’t want yes people.)

Your Sales Organization Doesn’t Need Direction to Sell More

Telling your sales team you want them to sell more is like telling the accounting staff to produce better financials. It’s their job and they know that. Yet, I’ve observed many leaders providing pretty much this guidance. That sums up much of the motivational feedback for too many leaders.

But there is another, better option. Leaders can instead take a more strategic angle to influence improvements by:

1)     Focusing on developing talent by strategizing on opportunities, observing sales calls, and debriefing after a meeting to provide feedback.

2)     Investing in practice time to improve skills. Don’t make them practice new skills on new opportunities.

3)     Providing input on how to bring value into sales interactions in a way that’s connected to strategy.

Sales teams need strategic direction and guidance on execution. They need to be given opportunities and space to be creative and strategic. But they don’t need to be told to sell.

You can find more insights into how to be the leader your sales team needs in my Harvard Business Review articles 3 Ways to Motivate Your Sales Team - Without Stressing Them Out and Sales Teams Need More (And Better) Coaching.

Current Read

I may run the risk of having a mindfulness section for the newsletter if I continue to talk about it. But I’m watching it’s importance in my life and how mindfulness – or perhaps more accurately, lacking mindfulness – pulls me out of high performance in every area from family time, to work, and even my alone time.

This Science News article discusses How Mindfulness-Based Training Can Give Athletes a Mental Edge that allows them to better focus during periods of high stress and improve their overall mental health. Read more about the benefits of mindfulness and how you might apply them here.

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LinkedIn Live

Join me on Tuesday, March 8th at 10 am Eastern for another live session. We will be discussing how to successfully disagree with the boss.