Thinking & Communicating Like a Boss

“Know any good books that can help with delivering solutions and not problems? My boss says I bring him too many problems, but even if I bring him an answer he just doesn’t want to be bothered with any day to day stuff. He basically said to only call/email him if there is a major problem. Never really encountered a management style like this before…”

I’ve encountered similar situations while working with companies through organization restructuring & realignment initiatives, but when a good friend of mine sent me this message the other day,  I couldn’t seem to think of a book that I’d suggest to addresses this situation. After thinking about it for a few minutes, I remembered an episode of a podcast I listen to that addressed this topic head on.

I sent my friend a link to the 6-minute podcast episode, titled “Sounding Executive”, suggested he check it out.  I asked him to let me know what he thought after listening.

The next day, I received a follow-up message:

“That podcast you gave me nailed it right on the head in regards to how to approach my boss. It made a ton of sense. I actually replayed a scenario from last week that went very poorly in my head, and used those 4 questions to assess it. I would have never even brought the situation to him if I’d known how to do this!”

I was excited to hear it & wrote this blog post to share with others who, whether they know it or not, are going through a similar situation.  While I highly recommend listening to the podcast episode for yourself, I’ve provided an overview of the problem & the solution below:


The Problem: Communication & Expectation Misalignment

1. We All Place Higher Value On What We’re Personally Responsible For – Most of us talk at a level of detail that’s commensurate with our role and responsibilities within our company.

2. Front-line Employees Are Responsible For & Therefore Most Value The Daily Details – Front-line employees see the day to day details. The root causes. So these details are very important…to them. And since these details are important to them, they often feel the need to share these details to corroborate and / or justify their actions or decisions when reporting to management.

3. Senior-level Management Is Responsible For & Therefore Most Values The Results & Outcomes – Senior-level management is responsible for & therefore most interested in end results and outcomes. The specific details that got them to these results are important, but not the focus. They’ve hired a team with the knowledge, skills & experience to make day to day decisions, and do not have the time or energy to constantly question or validate their hiring decisions. So, when they ask for an update, they’re typically asking for an update at their level – the results & outcomes level.

4. Both Sides Inaccurately Assume That, What’s Most Important To Them Should Be Important To Others– Front-line employees and senior management have a hard time understanding why the other doesn’t seem to understand or value their level of detail (or lack of detail) provided during status updates. Front-line employees often see their management daze out and lose interest during status updates. Senior level management views the overwhelming detail as a waste of time & doesn’t understand why the front-line employee can’t just “get to the point”.


The Solution: Ask These 4 Questions

1. Does my manager really need to know this? Before providing a status update, ask yourself, “Why am I telling them this now?” If you’re unable to answer this for any of the details you intended to include in your update, cut them out.

2. Am I providing detail at my level of interest or my manager’s level of interest? Try to think at your manager’s level. What are their responsibilities and interests? Your updates should be edited to address their responsibilities and interests, not yours.

3. Is my status update concise & to the point? Speak in bullet points to stay on task & to avoid rabbit holes.

4. Am I trying to prove that I’m competent and qualified? Provide details when asked but not as a default. Assume that your manager trusts that you have the right knowledge, skills and experience to make the right decisions. They will ask for the details they’re interested in.


I’ve listened to almost every episode of “The Look and Sound of Leadership” podcast, and several of them have been helpful to me, personally. But the “Sounding Executive” episode, specifically, has been a game changer. Not just for me and for the impact it’s had on my communications and expectations, but because of the impact it’s had on my friends, colleagues and clients that have encountered similar situations.

I highly recommend checking out “The Look and Sound of Leadership” podcast for yourself. If you do, be sure to check out the 6-minute episode that inspired this blog post, titled “Sounding Executive”, found here: