Five Suggestions for When Your Boss Needs Leadership Help

Typically undeterred from taking on a tough challenge, this week’s Leadership Chat on Twitter will focus on something we’ve all struggled with at one time or another: what to do when your boss needs help as a leader.

This isn’t an easy topic because it has so many layers:

  1. Simply by feeling this way you’re acknowledging that you want something to change; and change is rarely easy
  2. Recognizing that someone needs help requires a personal decision about whether you want to be the one to talk with the person about it
  3. Asking someone to change can easily bring on feelings of defensiveness and insecurity; which must be eloquently maneuvered or avoided in order to move forward.
  4. There is inherent risk; risk of loss of the relationship, a sense of trust, or perhaps even your job
  5. There is also opportunity for tremendous gain and personal growth

Given all these layers, what’s the best way to approach it? We’ll ask all of you to share your stories and experiences regarding what’s worked well, and not so well, at Leadership Chat tomorrow night.  In the interim, here are my five suggestions to get you started:

1. Spend some time clearly articulating on paper what kind of leadership help you believe your boss genuinely needs. Obviously, you have to take all of the emotion out of the situation to really be fair about this.  Let’s face it, generally when you’re feeling like you have a “bad” boss there’s typically some underlying emotion there.

Let go of the emotion and write down exactly what you’d like to see your boss do in regard to improving their leadership.  Aim to genuinely help, and don’t move forward until that is truly your objective.

2. Come up with three realistic ways your boss could make the change you’re requesting.  For example, if you believe your boss needs to stop micro-managing and trust you/your team to accomplish your own goals, then structure a plan that can be proposed for how to build trust and get to that point.

By arming yourself with realistic, thoughtful solutions you convey a sense of seriousness and commitment.

3. Think about whether you’re the right person to have this conversation with your boss.  Some people will never be comfortable having this conversation, but if you want to see real change take place it may simply have to happen. If there is an HR department to turn to for help, that may be a good option to consider.  For those of you without a formal structure within which to work, you may simply need to give a lot of thought to a way to have this conversation without making your boss feel threatened.

Words matter. Your approach matters. Your decision here is critical. Choose the right person and the best approach that creates a non-threatening atmosphere.

4. Be ready and willing to support your boss and make changes yourself, as appropriate.  If your own approach has made it difficult for your boss, admit it and be willing to change.  If you have responsibility for part of the proposed solution referred to in step#2, outline how you’ll be fulfilling that responsibility.

Remember, the more successful you help your boss become, the more successful you will become.

5. Tap into valuable resources and share them with your boss in a helpful and subtle way.

For example, Les McKeown’s book Predictable Success is brilliant for helping leaders get clear on the right steps to take at different phases in a company’s life cycle.  If your boss is struggling strategically and tactically, this might give them the insight they need to step up their leadership.

If your boss needs to understand and embrace the critical importance of loving your customers – and you, the employees – then share with them this brilliant book by Brains on Fire on the importance of bringing love into business, and this eye-opening blog post by Mack Collier on the difference between how companies market themselves vs. how rock stars do.

If your boss is an introvert, I’d be honored if you’d share with them my Introvert’s Guide to Leadership – it may give them some tools to help them move beyond their comfort zone.  And if you’re an introvert working for an extrovert this post should definitely be shared with your boss.  Of course, I hope that many of the posts here on my Visionary Leadership Blog will be of value to you and your teams!

These are just a few examples to get you started.  In sum, find great resources, talk about how they’ve helped you, and share them with a genuine desire to help your boss excel in their role.

What are your ideas? What’s worked well for you?

Steve Woodruff and I will be addressing these questions and more when we host the next not-to-be-missed edition of Leadership Chat on Twitter tomorrow night, September 13th at 8:00 pm Eastern Time.  Please join us!


Need help defining a business vision, purpose and mission and the strategies to support them? Hire me for Visionary Leadership programs, and work with me by emailing me at [email protected].



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Photo is Help! by Dimitri N.


  1. I disagree with the approach you’ve outlined here. I would suggest that this kind of “I need you to be a better boss” conversation is simply not have-able unless there is already a robust foundation of trust and understanding, in which case, the conversation is not likely to be needed.

    Disagreements over decisions and management methods are better discussed in the context of the actual facts. For example, saying “I’m struggling to understand why you made that decision, because it seems contrary to what we’re trying to do here. Can you clarify your thinking for me so I can understand?” AND then be open to seeing another, perhaps more informed, point of view.

    At the very least, the discussion should focus on facts and actual behaviors/decisions rather than feelings.

    In the case of micro-managing – it’s usually due to a lack of information or feedback, or pressure from above. One possibility is to say, “You seem to have a lot of questions about this project. I really want to give you the information you need to be comfortable with our progress. How can we do that? Would some sort of visual display help?”

    Again, the focus is on facts. Actual work. Actual decisions. Actual behaviors.

    Giving your boss a book to read on Leadership is like giving your wife a book to read on weight loss. Bad idea.

    • Hi Linda,

      I think we actually agree on more than you might think. It’s very possible that the person will just not be able to have the conversation, which is why some other approaches may need to be considered, but in my experience even if there is a strong, trusting relationship that doesn’t mean there won’t be challenges that should be discussed.

      I absolutely agree with you that when you go in with a plan or approach it should be based on facts and not on emotion, and you have some great suggestions on how to handle the conversation of micro-managing in particular.

      And I think there’s a big difference between saying, “Honey, I want you to read this book on weight-loss” and, “Joe, a colleague of mine in another industry suggested this book called Predictable Success and it gave me some new ideas on how we can manage through our current business cycle. May I share it with you?” So much has to do with the approach, and with genuine respect for the other person.

      I hope you’ll join us for Leadership Chat tomorrow night – would love to have you there sharing your insights! All the very best and thanks so much for the comment!

  2. @Linda – I agree that you must have an established relationship in order to have a meaningful conversation, like how each can improve. I have had those discussions throughout my career. I have used much of the techniques that Lisa outlined in her blog post. I like your statement on “Again, the focus is on facts. Actual work. Actual decisions. Actual behaviors.” That is what it is all about.. Which if done right, will make going to WORK a lot more enjoyable.
    Steve Bell´s last blog post ..10 Years Later

    • Steve,

      Love that you and Linda have really zeroed in on what makes this work – thank you so much for that and I hope to see you tomorrow night at Leadership Chat as well! All the best.

  3. Thank you Lisa for the link and mention ;) I like your Point #2, no one likes hearing ‘Your way is wrong’, instead if you can spell out how they and the company could benefit from another approach, that’s more likely to change the boss’ mind!

    See you tomorrow night at #LeadershipChat!
    mack collier´s last blog post ..Think Like a Rockstar is coming to Atlanta and #SMIATL this weekend!

    • You’re welcome, Mack! And I couldn’t agree more; hearing something akin to, “Your way is wrong” is the quickest way to get someone to tune out. So glad to know you’ll be joining us tonight for Leadership Chat, see you then!

  4. Hi Lisa,
    Very unique topic — not often addressed in leadership blogs.

    Your treatment of it is on target for it considers the many layers. I especially like “consider if you are the right one” to offer this conversation.

    I like the addition that Linda (above) suggests — the more specific you are the in building the awareness instead of declaring it, the more likely the success.

    Here’s a post by Mike Figliuolo at that might expand this engaging discussion further:

    8 Ways to Tame a Terrible Boss

    Thanks for this thought provoking post on such a sensitive subject Lisa.
    Kate Nasser, The People-Skills Coach´s last blog post ..Leaders, Realizing & Mentoring Someone’s Dream

    • Hi Kate,

      Thank you so much for the kind words and for sharing Mike’s post with me. I’ve been working to set a date for him to Guest Host on Leadership Chat – so it’s very timely! And yes, I agree with you and Linda about being as specific as possible; it certainly helps to not only focus but take the emotion out of the situation as well.

      All the best and hope to see you tonight at Leadership Chat!

  5. Everything always comes down to one simple fact:

    It’s not WHAT you say, it’s HOW you say it!
    Kirsten Wright´s last blog post ..Is the right hand talking to the left?


  1. […] sure to read Lisa Petrilli‘s take in her post, Five Suggestion for When Your Boss Needs Leadership Help. Add Lisa’s five to my eight, and you’ll have 13, before we even begin getting more […]

  2. […] >> Five Suggestions for When your Boss needs Leadership Help by Lisa Petrilli […]

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