How to Win Friends and Influence Bosses

Hint: You Get What You Focus On

The other day I was speaking with a good friend who is a division manager in one of the companies we provide help to. It’s a small software company that’s been experiencing steady growth for several years, and through that growth, strain is beginning to show in inconsistent results and in all the ‘grass fires’ of discontent from their clients that keep popping up.

“It drives me crazy!” she said. “On one hand the owner wants more and better results, and on the other hand he won’t hold anyone accountable. How in the world are we supposed to succeed when people don’t have to follow the systems we set up to succeed? And worse yet – every time I try to talk with the owner about this problem, we get buried in the ‘quick, easy’ stuff and never get to the really important issues. I’m starting to think that the owner just doesn’t want to deal with the real issues and is simply avoiding them as fast as he can!”

Perhaps you can relate or have had someone you know in a similar situation. My friend wanted to know how speak with her boss in a way the boss would respond, not only for her own benefit but that of the entire company – including the boss!

Focus on outcomes – the company / both of you, the boss, and you

If you want to get to real results, keep your attention on the outcomes you are trying to achieve. I can’t tell you how many times I’ve been in a meeting and part way in flummoxed the group by simply asking “So what do we most hope to achieve by the end of the meeting?” We are a culture of action, of getting things done! And I love to see that energy channeled in a direction that benefits everyone. (A nice side effect is that friction between people trying to achieve incompatible outcomes goes way down when we set a clear mutual goal!)

If you additionally want to be perceived as trustworthy, focus first on the outcomes of the broader organization or relationship, then on those outcomes you would like for the other person, and finally on the outcomes you want for yourself. It takes some practice, yet the results are very rewarding. I guarantee if you to work to speak first to what the business needs, mention what you think the boss needs, and wrap it up with “and here’s what I need to make that happen for you and the business” you will have a much more receptive audience.

Hint: if you start getting pushback, confirm each desired outcome from the top down. “I was thinking that [insert goal here] was what the company really needs to have happen. How does that match with what you’re thinking?” Then confirm the boss’ needed outcomes “Here’s what I think you need out of this…” and finally state the outcomes you want for yourself.

Actions you can take today

  1. The next time you interact with your boss, before you begin speaking (or better yet before you walk into the room, pick up the phone, or start typing that email) think about the outcomes you most want for the boss, for you, AND for you both. Get it clear enough so that you could write them down on his or her office whiteboard. Share that desired mutual outcomes with your boss upfront – “Here’s what I’d really like as outcomes for you, the company, and for me…how does that fit with what you’re thinking?” and enjoy a more mutually beneficial discussion.
  2. Try the above with anyone you interact with – family members, neighbors, co-workers. It’s a skill that, once learned and applied, will have people wanting to have you on their team as you will be able to help get a clearer view of the big picture while simultaneously getting better results.

Chris Hutchinson

About the Author:  Chris Hutchinson, President and CEO of Trebuchet Group, helps facilitate leadership growth and business success of local and global clients, using a collaborative approach to enable consistent, effective results. He can be reached at

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