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Crucial Conversations for Accountability

Dealing with a Last-minute Boss

Dear Crucial Skills,

My boss likes to leave things open for change until the last moment and this stresses me out completely. A few examples:
(1) We were presenting to senior management and had agreed to drop several items from the presentation based on specific logical reasons. Two hours before the presentation, he decided we needed to add those items back into the presentation without reason.
(2) We were launching a high-visibility product—from senior management’s perspective—and he tried to change the launch material that was already delayed going into production. If we had done as he wanted, we would have missed the launch deadline and faced huge embarrassment.
(3) We were in the middle of an event and he texted me asking to change the schedule during the event!

Situations like these are causing immense stress for me. I like to plan things well in advance and do not like surprises at the last moment. How can I successfully communicate this with him?

Stressed Out

Dear Stressed Out,

Great question! And thanks for sharing the detailed examples. Often we have to work back from our emotions to the story that drives them, and then to the facts behind our story. As I see it, you’re dealing with the following:

• Emotions: Stress and frustration.
• Story: “My boss likes to leave things open for change until the last moment.”
• Facts: The three incidents you describe.

Challenge your story. I want to begin by challenging your story just a bit. As humans, we often make what psychologists call “The Fundamental Attribution Error.” We attribute others’ bad behavior to internal dispositions (as you do when you suggest, “My boss likes . . . “), and ignore external factors that might be influencing his or her behavior. Take a bit more time exploring why your boss might be leaving things open to the last minute. Here are a few possibilities:

• He is distracted by other tasks and doesn’t really attend to your priorities until the last minute. Then, when he finally gets his head in the game, he wants to make changes.
• Other leaders he must accommodate don’t pay attention to your priorities until the last minute. Then they demand changes, and your boss passes them along to you—as if they were his.
• Perhaps some situations are so fluid that they really do require last minute changes. (I’d be surprised if this last one is actually true, but it’s worth considering.)

A robust solution to your problem needs to address all of these influences. If you focus too narrowly on motivating him, without acknowledging the reasons for his last-minute meddling, he’s likely to feel attacked and become defensive.

Determine what you really want. Focus on what you want long-term for the organization, your boss, yourself, and for your working relationship. Take pains to avoid a self-focused perspective (such as when you say, “Situations like these are causing immense stress for me. I like to plan things well in advance and do not like surprises at the last moment.”) Instead, focus on the benefits you want to achieve.

Trust me. If you are feeling stress, then others are as well. And the organizational costs of these last-minute changes can be profound. I’ve seen organizations grind to a halt, as managers stop taking action and making decisions because they fear others will second-guess them at the last minute. If you can introduce greater predictability and stability, you will be helping your organization, your boss, and many others—including yourself.

Establish expectations that work for everyone. In our Crucial Accountability course we teach a skill called Describe the Gap. The gap is the difference between what you expect and what you’ve observed. In your case, the gap is between what you expect and what your boss and other stakeholders expect. Your conversation will succeed to the extent you can align these expectations.

I suggest using principles and terms from project management best practices to describe your expectations. A good process involves the right people (your boss and other stakeholders) at the right times, before decisions become last-minute.

Learn how project management is done in your organization and use what you discover in the conversation. Your goal will be to have your boss and other stakeholders commit to following a project management process that will make their lives easier, and improve the effectiveness of the organization.

Move important decisions forward in time. Since the problem is that your boss isn’t making decisions until they are urgent, a part of the solution is to create this urgency earlier. Project plans are supposed to do this by establishing checkpoints that involve people early in the process. However, this involvement only works if people take the plans seriously—if the checkpoints create a sense of urgency.

You need to make sure you are getting people’s mind share and serious involvement when you need it—early in the process. If you can’t get serious involvement early, then count on getting it at the last minute.

Get permission to hold people accountable to the project plan. Your first test will come when your boss and others skip project checkpoints or arrive unprepared. Talk with them in advance about this potential. If they don’t get their heads into the project on time—as called for in the project plan—then the whole planning process will break down, and you’ll be back to last-minute changes.

Some organizations even introduce a shorthand way of referring to the negative cycle. One I work with calls it “Skipping the D” and “Hijacking the D” (meaning “Skipping the Decision” and “Hijacking the Decision”). Everyone knows what these phrases mean and they use them as reminders to hold each other accountable.

I hope that some of these suggestions will work for you. Let me know how it goes.


You can learn more insights and skills like this in Crucial Conversations for Accountability

17 thoughts on “Dealing with a Last-minute Boss”

  1. Kim


    In your reply, you broke down the email to “Emotions” “Story” “Facts.” I found this process very helpful along with your explanations later in your response. Maybe its been too long since I took the class, but I found the dissection helpful. In the future, could you all consider doing this when responding to questions?

    Thank you,


  2. Rivkeleh

    This was so timely! I have a very similar situation, and when I attempt a conversation on the subject, the response is either deflection by bringing up a non-work-related subject, often movies, or saying “I wish that were the only problem *I* have!” and then a discussion of “when you get to my level in the organization” that generally dismisses the concern as not important to the senior staff. I have been working on various ways to improve the situation, including a deep focus on changing anything I can see in my own behavior, story, or attitude that would make a difference, for several years. I wonder if its possible for a business to simply be so entrenched in this kind of behavior that they LIKE it — that there’s an emotional payoff that they’re not willing to give up.

  3. Sandra Shill

    I can identify with the writer, but I’ve come to learn that this style of business is, unfortunately, the “new normal.” It appears that, to succeed in today’s workplace, it’s vital to remain uber-flexible and be willing to cheerfully accommodate last-minute changes. There seems to be little place for those of us who might prefer to “plan things well in advance” — if we don’t adapt to this “new normal,” the company might well find someone else who will.

    So, while I definitely endorse all of David’s strategies to try to minimize last-minute changes, you’ll need to implement these strategies with great diplomacy and then, if you still end up receiving requests for last-minute changes, try and suck it up as best you can. I think the nano-second culture is here to stay (or even get worse), so we more “seasoned” folks (I’m making an assumption here about your age — please pardon me if I’m wrong) are stuck in the position of “adapt or die.”

  4. David Maxfield

    I agree with both Rivkeleh and Sandra. Many organizations have come to accept turbulence as the new status quo. I had one person describe his manager as a “heroine addict”–“She creates a crisis, so she can become the heroine who fixes it.”

    In Influencer we suggest that “the world is perfectly organized to create the results you are currently experiencing.” If your experience is turbulence and last-minute decision making, then look for the causes in all 6 Sources of Influence. For example:

    Personal Motivation. Some people are like the heroine addict who loves last-minute improvising.

    Personal Ability: Some people don’t know how to say “No” to last-minute stakeholders–or don’t know how to manage complex projects.

    Social Motivation: People are rewarded by others for working on what’s urgent, and discouraged from working on priorities until they become urgent.

    Social Ability: Stakeholders are slow to provide critical input–so decisions have to be put off until the last minute.

    Structural Motivation: Promotions and pay go to the heroine addicts instead of to people who prevent crises.

    Structural Ability: the organization doesn’t have a strong project-management function.

    There are likely to be multiple Influences in each of the Six Sources conspiring to maintain the status quo. Changing the norm will require solutions in each of the Six Sources.

  5. Susana Gonzalez

    I agree many turbulance occurs in high demand businesses and reading your concern. There is another way to deal with your situation if you already know what will be needed than prepare both outcomes whether one or the other is used. You already know that there is always last minute requests, have these request been accounted for prior to the final asignment, if so than be prepared. Not everything can be covered but this will reduce some of your stress. As David Maxfield mentioned sometimes is not your boss directly. It can be his superiors making the requests. Don’t centralized on the issue where it has become personal. The theory is more like we the company.

  6. alfranco17

    The Myer-Briggs theory splits people according to 4 dimensions, one of which is J/P. The J type feels anxiety by loose ends, and wants to make a decision right now and move on, never having to change it. The P feels anxiety when out of options, considers every decision as tentative, and reserves the right to change it at least moment if an opportunity comes up. The result of these two extreme characters dealing with each other is a lot of tension.

    If this is the case, you should be aware you think differently, and both have to make adjustments for the other. Neither will change. It is like sitting a right-handed person to the left of a left-handed one at a dinner. Either they take into account their differences, or they will elbowing each other all the time.

    1. Danny

      Mr. alfranco17 –

      You’re absolutely right!

      Although I’ve heard of Myer-Briggs, I’m not completely familiar with it.

      All I know is that when considering the “types” you mention above, Type P, who is quite often entrepreneurial and thus the boss and with that personality somewhat scattered absolutely needs the J Type. The challenge is for the Type P is finding a J Type who can really assist–and has the patience to assist–Type P in filling in the gaps–Type P’s shortcomings.

  7. Sandra Shill

    Just to clarify, my boss is not the problem. Her boss is not the problem. I’m not even sure my company is the problem (although I used to think it was). I just think that, as I said earlier, this is the “new normal” in corporate America (or at least in publicly held companies), so there’s not a lot that knowing those “6 sources of influence” is going to do to make meaningful change, unless the problem is generally localized to a particular boss, department, or, maybe division in one’s company.

    I don’t mean to sound negative – to the contrary, finally surrendering (mostly) to the new reality has actually brought me some peace, especially since the demand for high quality has decreased as the demand for greater flexibility and shorter time frames has increased. (If that weren’t the case, the situation would be hopeless.) When I think about it, it does depress me (because I’m someone who really values quality and generally finds it painful to produce “good enough” work), so I just try not to think about it too often LOL!

  8. Rivkeleh

    Sandra, I take it as part of my responsibility to state what I believe the cost of the change is, and trust that they are willing to accept the cost, if they request the change. Like you, I’d rather decide earlier (I’m a J on MBTI), but if the payoff of “being too busy to pay attention to these things” is worth more than the cost of the late-breaking decision for whoever is making it, unless it’s my company, like you, I just need to trust them and make the change as instructed.

  9. Engela


    I am in more or less the same situation. In my case, projects would be planned and my involvement in the project will only made known closer to the deadline. I have had to do rushed jobs, while colleagues had come prepared, and I had fallen short of the standard. When I raised the issue with my boss, she said that I should have known about these projects by finding out about it myself. Surely a manager cannot expect me to find out for myself? This poor communication system is evidence of a disfunctioning team.

    1. sandrashill

      Sounds to me like you’re both kinda right….

      Yes, if communication were better, the project manager and/or your boss would have made sure that you were involved sooner. However, if you want to ultimately work towards becoming becoming a higher-level player, you do need to find ways to be more “connected” to what’s going on (what new projects are starting up, what the priorities are for your team, division, and organization, etc.) and proactively inquire about new projects/initiatives to see whether/when it might make sense to get involved in them. Learning to see the “big picture” and take initiative is one of the things that typically separates more order-taking “junior” employees from more proactively involved “senior” employees.

      1. Engela

        Thank you. This is giving me some perspective

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  13. Suzanne

    This insightful blog post provides valuable advice on navigating disagreements with your boss, a delicate yet crucial aspect of professional communication. By emphasizing timing, positivity, empathy, and respect, it guides readers on effectively voicing dissent without jeopardizing their well-being or career. A must-read for anyone looking to improve workplace dynamics.

  14. jackson

    Addressing last-minute changes at work can be challenging. Consider having an open conversation with your boss about the impact on productivity and propose a collaborative project management process. Emphasize shared goals and the benefits of a structured approach. Good luck!

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