How to Coach Your Boss

Much has been written on the topic of coaching employees. (One of my favorites is a book we published a few years ago by Daniel Harkavy. It is called Becoming a Coaching Leader: The Proven System for Building Your Own Team of Champions.) But very little has been written on the topic of coaching your boss.

A Discussion Between Two Co-Workers - Photo courtesy of ©, Image #2306439

Photo courtesy of ©

The truth is that most employees see things that their boss says or does that are ineffective or inefficient. Sometimes, they see these things more clearly than anyone else. The boss could profit greatly from the insight of his or her subordinates—if only they could get honest feedback.

The problem is that most people are scared to correct their boss or offer advice. They are afraid they will be punished or, at the very least, given a cold shoulder. But that’s not always true.

The best bosses welcome criticism, knowing that the shortest distance between where they are and where they want to go is the truth. They create a “safe environment,” where people can freely speak their mind.

But what if you are not sure about your boss? What if you are afraid you will jeopardize your career by speaking up? Here are a few things to consider when attempting to offer advice to your supervisor.

  1. Check the weather. Bosses are people, too. They have families, pay bills, and struggle with the same things you do. They probably have a boss as well. They have good days and bad. And, sometimes they are more receptive to input than others. Find a time when the boss is not in a bad mood or distracted by other things.
  2. Be humble. Don’t correct your boss out of anger. Don’t correct him out of pride. Instead, acknowledge that both of you are human. He or she has faults—but so do you. The reason you are on the same team is so you can help each other.
  3. Start with praise. Most people can hear criticism if they know they are loved and accepted. Offering a genuine compliment is a good way to start a difficult conversation. But beware: it must be authentic. Otherwise, it will feel like manipulation.
  4. Ask for permission. You might say something like, “There’s something I’d like to share with you that I think would be helpful to both of us, but I want to make sure I have your permission to speak openly.” Then pause. It’s difficult for the boss to take offense if he or she has given you permission to proceed.
  5. Put it in context. One of the best things you can do is help your boss understand how his behavior is keeping him from accomplishing his goals. For example, “I know that collaboration is one of your highest values. But when you cut me off in mid-sentence, it makes me want to withdraw and not participate.” Or, “You have always encouraged me to set high goals and believe in myself, but when you snap at me like that, I feel small and want to give up.”
  6. Assume the best. I don’t know too many bosses that get up in the morning with the goal of making their employees miserable. They are most likely clueless about the behavior that is driving you crazy. If they knew about it, they would correct it. You have to assume they will change once they have the benefit of your perspective and input.
  7. Believe that it matters. It’s not an accident that you are working for this person at this time and are noticing this behavior. Maybe God has placed you in this person’s life to help them grow. Some of the very best counsel I have ever received came from my subordinates. If you don’t speak up, who will?
  8. Take the risk. Speaking out takes courage. You will never grow into the leader you were meant to be if you are not willing to take a risk and occasionally speak up. Being a suck-up will not get you promoted. Being courageous eventually will—so long as it’s done in the right spirit.

As a boss myself, I consider it an expression of loyalty when my people talk directly to me rather than about me. I know I have faults. I want to grow. You can help me—and your own boss—by taking the initiative.

Question: Do you need to sit down and have a talk with your boss? You can leave a comment by clicking here.
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  • Shari Brown

    Thanks for the encouragement and the reminder. Sometimes it is easy to forget that our bosses operate from a human perspective. What are your feelings regarding socializing regularly with your boss or employees?

  • Michael Hyatt

    Personally, I’m all for it. The more people like one another, the better they work together.

  • Bowden McElroy

    Re: Start with praise. Just make sure it isn’t the only time you offer praise. Otherwise, every time you give a compliment people will wince.

  • http://www.BUSINESSSANITYBLOG.COM/business_sanity_blog/2007/06/coaching_your_b.html Business Sanity Blog

    Coaching your boss

    As you may know I’m a big fan of Michael Hyatt, Pres. and CEO of Nelson Publishing and his blog From Where I Sit. His recent post entitled: How To Coach Your Boss really hits the nail on the head

  • Benjamin Lichtenwalner

    Trust or Leave: It all begins with trust. If you don’t trust your boss to take the feedback positively, when you follow these excellent steps, then you are in a bad working relationship and it’s time to move on. For more on the critical role of trust in a team’s success, I also recommend the book The Five Dysfunctions of a Team.

    Put Yourself In Your Boss’s Shoes: I wrote about a Day in the Life of Your Boss to reflect the importance of this for employees. When you understand their perspective, it’s always easier to give feedback in a manner that is positive and well received.

    Begin with Your Own Faults: Finally, an outstanding resource on how to give criticism in general is the timeless classic by Dale Carnegie – How to Win Friends and Influence People. Your recommendation on beginning with praise is a key point he also covers. In addition, Carnegie suggests talking about your own mistakes first. For example, I’ve learned to begin with statements like, “I’m still working on this myself and so it’s a bit more clear to me when I see you do…”.

    Excellent post, Mike. It’s so rare that people tackle the challenge of “influencing up”. There is a special delicacy to these situations that few people have answers to. Yet, the tips you provide here are fantastic. I’ll definitely look to apply them at my office. Thank you so much for sharing!

    • Michael Hyatt

      Thanks for sharing these additional resources, Benjamin. Excellent!

  • Cyberquill

    First I need a boss. Then, of course, I’ll need to sit down and have a talk with him or her regarding his or her manifest shortcomings as far as selecting competent employees. 

    • TNeal

      In others words, no, you don’t need to sit down and talk with your boss–which is also my answer. Need one to know one. :-)

    • Robert Ewoldt

      Ha ha!

  • Paul Coughlin

    Oh boy – I wish I had know those things years ago :-)

    I learned the hard way that how you deliver the message, is at least as important as the message..

    Reflecting on what you’ve written Michael, it reminds of the old adage that “people don’t dislike change, they dislike being changed”..

    If we understand what their goals are, and share insights with them on ways they can grow towards those goals.. they will appreciate what we have as valuable, and thanks us.

    If we simply show them where they are wrong, they may well thanks us begrudgingly on the surface, but inside they will experience it as criticism, triggering resistance, and threatening their internal homeostasis.. stress response..

    Your bullet point summaries are great Michael…

    There is a strong sense that all of these posts would make a brilliant book!


    • Michael Hyatt

      Thanks, Paul. You never know. It may find its way into a book someday!

    • Benjamin Lichtenwalner

      “people don’t dislike change, they dislike being changed.”

      I don’t recall hearing that before but it is simple wisdom that is spot on. Thank you for sharing it Paul! That is one I will definitely remember.

      • Paul Coughlin

        I think that actually came from Bob Proctor originally – and I loved it too  :-)  

  • Ianmspence

    This is making me think. Thank you.

  • Kelly Combs

    This is a great post, Michael.  As a former executive assistant to the chairman of a Fortune 500 company, I know that at least in my case, my boss welcomed input.   Being humble is certainly an important step, and if you approach it in the right way, who wouldn’t want an opportunity to grow?  Well, only someone whose ego is too big to realize they need improvement.  There is the issue.  How big is your boss’s ego?

    • Robert Ewoldt

      And if you listen to Jim Collins, the biggest differentiator between a good leader and a great leader is humility.  If someone’s serious about becoming a great leader, they should want to practice or cultivate humility, part of which is realizing that they need constant improvement.

  • Chrisjohnstoncoaching

    Good stuff. 

  • Heather Stagl

    Your post shares many of the points I wrote in a post a couple of years ago called “How to Deal With A Clueless Boss,” which includes 10 tips for giving leaders feedback.

    One I would add is: Don’t make it a mutiny. Represent yourself and your own observations. Unless you have permission to represent a group, don’t bring anyone else into it. Let others speak for themselves, otherwise you are effectively throwing them under the bus.

    • Michael Hyatt

      Great counsel. This is an important point.

    • Robert Ewoldt

      Yes.  And especially don’t ambush your boss in a staff meeting or something like that :)  That might not get the best response.

  • Chris Patton

    As usual, great post on an unusual topic!

    I love the “Check the Weather” point!  My boss (also my father!) is no longer involved in the family business, but trades in stocks.  I make it a habit to check the stock tickers before heading into his office for a visit!  If the DOW is down, I postpone the visit until another day.  I love having an easy indicator of his mood right there on my computer screen all day long!

    As a boss, I also love the “Take the Risk” point.  I am looking for those associates that will step out and take a chance when they really believe in something.  Even if this means I may be offended, they are showing courage that is too often absent in these days of political correctness!

    Thanks for the post!

  • Anonymous

    This is something I struggled with during my first several years of employment.  I have had the privilege of working for some very talented, Godly individuals.  Some of them, however, did have a blind spot that limited their total effectiveness.  In retrospect, I wish I had had the courage to address some of those issues, but too often I used my relative youth and inexperience as excuses.  
    The biggest takeaway I have from your article today is that I need to create an atmosphere that allows individuals to approach me and provide constructive criticism.  I’m not sure that this type of atmosphere currently exists.

  • Chris Patton

    I agree with you Karl.  I got some tremendous feedback just over a year ago when I had an independent company conduct a 360 degree review for me.  They sent an extensive survey to 15 people I selected.  It was a mix of my direct reports, my boss (and father), my partner, several peers from our industry, and a couple of former employees.
    The results were anonymous, but grouped according to category (peer, direct report, supervisor, other).  I think that had a lot to do with the candor of the feedback I received.  I was shocked at how much feedback I actually received!  I will be doing this again in a couple of months.

    I spent a full day offsite (in the local library) studying the results and formulating a plan to correct the weak spots.  Some of it was not new to me, but some of it was.  There was also some sincere positive feedback which surprised me (very intense and well thought out).

    If we can create an atmosphere that will promote this kind of feedback on a regular basis, we will come out way ahead!

    Michael, please follow this up with a post to the bosses that tells us how to create this kind of atmosphere!


    • Robert Ewoldt

      Chris, this sounds like a great exercise to do as a leader.  I’ve heard of people doing this type of thing before.  Do you feel like it was worth it?  Have your relationships with your co-workers improved?  Since you’ve made some changes to the way you do things, do you feel like they trust you more?  Or that they’re more comfortable coming to you?

      • Chris Patton

        Robert, I did not have to pay anything for this the first time, but it was such a good exercise that I will be doing it again (and paying!).  It took time to set up and execute, but it was definitely worth it!

        My relationships with those around me has definitely improved!  In several cases, my ongoing feedback improved because they saw I was serious about seeking it AND using it…which leads to the trust you asked about. There is definitely more trust.  

        While I am not naive enough to think I am now getting all of the honest feedback I want on a daily basis, I do see more of it than I did before.  We meet in weekly one-on-one’s and I get more direct feedback in each of these now.  I did not get much of that before.

  • LOALoveCoach

    Love this post.  These are concrete suggestions that really work.  When my boss makes a suggestion or decision that slows me down, I say, “May I offer you another perspective?”  She always says yes which opens the door for me to respond respectfully.  I always keep one thing in my mind, my bosses ultimate goals.  Then I state my needs with meeting those goals in mind.  Thanks again Michael, I learn so much from your blog!  Catherine

  • Alan Kay

    This is an important issue in all organizations. Upward transparency enables greater effectiveness and productivity. All management development courses should include skill development on taking input from staff.  
    Another point – enlightened senior people now engage in reverse mentoring. They want to learn things from younger people, an obvious example being social media. Giving your boss feedback should be seen a learning opportunity as well an attempt at corrective action.

  • David Adeola

    This is a fantastic piece which I’ve already shared and I believe the Key issue is trust and the willingness to be humble and sometimes those attributes are not possessed by most bosses!

  • John Lambert

    I have found it helpful to own everything up front when approaching about a delicate subject.  I would say, “This may totally be my own misunderstanding, and if it is, I am willing to own it completely…”  This gives room instead of putting your boss into a corner.  

    Another thing I try to remember is that there is a difference between having a question and being questioning.  It all has to do with attitude.

    If we have built up what John Maxwell used to call, “relational change in the pocket”, through consistency, trust, and loyalty, I believe that we will have the boss’s ear when we really need to give constructive criticism.  

    Thanks for this post Michael.  The last thing a leader needs is either “yes men” or “rude men”!

  • Kelly Chadwick

    These were excellent points.  I have an incredible staff that regularly bring me feedback and I am a better boss and leader because of it.

    Another strategy that makes it easy for me to receive feedback from them–they regularly offer encouragement and support as well.  Your first point mentions that bosses are people too.  It is way easier to offer suggestions for growth (which could be an emotional withdrawal) when you’ve regularly made deposits along the way.  Because my staff do this well (and I hope I do too), we’ve created a safe environment for all of us to give and receive correction when necessary.

  • Wayne Hedlund

    Great article! I’m going to forward to my staff as a reminder to them that I desire to be approachable and teachable. 

    Regarding point #3: I really appreciate the idea that ‘Creating Safety’ should be a key element whenever you confront someone from the book Crucial Confrontations. When people feel safe regarding the relationship, they are so much more open to input and advice.

    I would also recommend adding one more point: 

    LEARN THEIR FRAME OF REFERENCE: Daniel and the chief of staff so perfectly illustrate this. It wasn’t until Daniel learned his frame of reference that they were able to work together towards a solution (that is, if Daniel’s leader let him eat what he wanted, he (his boss) would be in BIG trouble!)

  • Amy Hunt

    I have learned how to do this with my boss and he’s incredibly appreciative of me. What I hadn’t thought about, though, is that I could be important for *him* at this time in his life. Usually when I’m perturbed at work I think about how I can grow and honor God by accepting all circumstances. But giving my all to encourage and help my boss to see a different perspective could be my worship, too. Such good stuff here. 

  • ThatGuyKC

    This is so helpful. As an individual contributor my opportunities to lead are limited, but I try to coach and encourage people within my sphere of influence whenever I can. In the last year I’ve sort of dabbled with coaching my boss through our 1:1 meetings and sharing articles (mostly from you and Seth Godin). It’s been mostly positive, but I’m trying to be more strategic and impactful. Thank you for the guide.

    What was the most difficult piece of feedback you received from someone who worked for you?

  • Jill

    While I can see all of this as applicable with a godly boss, in an emloyee’s market with a highly valued employee, I’m going to struggle implementing this. (I’m still struggling with a previous post about not talking about the boss’ faults to others, in both my day job and a ministry setting, so I recognize I have a ways to go myself. I feel in both arenas sometimes like the book title I saw once, “No Turn Unstoned”. Sometimes I just need to vent/commiserate when the frustration level gets intolerable. So I’m still working on me, too.)

    Our engineering/construction company branch has really felt the impact of the economic downturn, having laid off two employees 2.5 years ago and not replacing two who retired/quit. The boss is completely stressed out (having been promoted when his predecessor retired) handling the additional duties the other (godly) man handled so well, so talking to him about things is a total mine field. There appear to be no “good days” to offer constructive criticism, and I fear always for the “ax” to fall should I say anything.

    While the day-job boss at least usually keeps it private – emails and one-on-one conversations – the ministry leader (a godly woman!) occasionally openly criticizes couching it under the umbrella of “refining” (and training for the others present).

    While I don’t negate everyone else’s “Great Article, Michael” I fear it’s just going to take me a while to be able to say it worked for me in my situations.

    • Wayne Hedlund

      Wow. Sounds very difficult. I recommend you check out the book called “Crucial Confrontations”. It does a superb job of outlining how to approach and address difficult people and still have a high potential for resolution at the end. 

  • John Richardson

    While I agree with your post Michael, in my situation I don’t think it would be possible. I think a certain degree of trust is necessary to make this work. As Ben said, it’s trust or leave. The problem is the economy. While it used to be easy to go elsewhere, it’s now almost impossible in my field, with the current state budget. I’m sure there are lots of people in similar situations.

    • Robert Ewoldt

      I think there are probably a lot of other people who believe that they are in precarious positions as well.  Even in a bad economy, though, people who receive feedback are the people who are the most effective leaders, and the ones who lead the most competitive companies.

  • Joe Lalonde

    Sometimes I feel like I want to sit down and talk to my boss about some issues that bother me. Things like not responding to emails or not getting back with me regarding purchasing issues.

    However, I am never able to work up the courage. Being raised to believe a boss can and will fire you for any small reason has made me really reserved at work. It’s something I need to work on and I believe it’s something God has been dealing with me about lately. Books, blog posts, etc that talk about stepping up at work have been showing up in my life.

  • Robert Ewoldt

    It’s nice when you have a set time each week, or every other week, with your boss, to sit down and talk about what’s going on in the office… questions you have, suggestions, etc.

  • Ron Harvey

    I think this is possibly the single most missing element in leadership . . . honest, constructive feedback!

  • Victoria Bakken

    I am in a masters program on  Organizational Leadership and we are in the process of reading Primal Leadership. One of the five discoveries mentioned in this book talks about the CEO disease. It speaks about leaders wanting feedback from thier those they lead, but there is a problem with those people beliveing thier leader can change. Often times people don’t want to go through the trouble of bringing up things to thier leader if they don’t believe they can or will change anyway.  
    Of course on the flip side, leaders can learn new tricks.  So maybe the issues lies in people needing to believe and trust more in leadership    

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  • Stuart Loe

    Actually, I do not need to sit down and have a talk with my boss.  My boss regularly seeks my counsel on matters personal and work-related.  I don’t know why he thinks my opinion or wisdom are worth seeking out, but it is flattering.

    The only time I might need to man up and confront him is when he is really excited about an idea that I think is bad or not worthwhile.

  • Brad Bridges

    I especially appreciated the the two about assuming the best and checking the weather. Tough as it may be to do so, when we put ourselves in their shoes it can really change our perspective to see they are normal people and go through normal struggles. 

  • Officialbsj

    One cannot know how to lead if you have not followed, but you can follow without any leadership experience. This suggests that leaders would do well to heed the cautions and critiques of their subordinates, since these subordinates are slowly gaining the needed experience and insight to assume leadership roles. Leaders (often mistakenly called bosses, lol!) need to understand that to take to heart the views of subordinates, and to act positively on constructive criticism doesn’t just safegaurd the employee, but it secures the leader’s job…

    • Michael Hyatt

      That’s so true. I once worked for a man who wouldn’t listen to his subordinates, including me. Eventually, I was promoted over him and became his boss. After three months, I fired him. He didn’t get it as a leader or a follower.

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  • Jrosecox1

    I love all of the comments and suggestions here.  I have a newer boss who is also new to the company, technology and the field we work in.  He told me he was a micro-manager and that is just how he did things and has consistently put his name on projects I am working on but has not produced one of his own.  Additionally, when he came on board, he changed my HR label to read “Junior”.  I have got to his boss and one additional layer but have met with the first one saying, “You will need to learn how to figure it out” and the other saying “My hands are tied”.  I have been with this Fortune 20 company for over 12 years and have no desire to make any changes.  HELP!

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    It’s important to put the stuff elegantly in te right context.

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