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My boss and I take work trips once a month to pitch new business to potential clients. We’ll usually go out for dinner after the day is over, during which he’ll always debrief about the day and talk about what we could’ve done better. I think these are conversations that should be happening during work hours, especially because I can strategize better when I’m not exhausted at the end of the day. What’s the best way for me to create stricter boundaries during these work trips?


Bruce Sandy, principal, Pathfinder Coaching, Nanoose Bay, B.C.

I appreciate your desire to protect your personal time and set clear boundaries with your boss when you are on work trips together. This is an opportunity to continue to consciously design your relationship with him. Because it is your boss, there is a power differential in the relationship. He has a different work style than you and he is setting the tone for your work trips. To address this, try the following steps:

  • Acknowledge: Tell your boss how much you admire and appreciate his interest in and dedication to the work and how he wants to help you improve in your position.
  • Be curious: Ask your boss about when he is more energetic, how he balances work and life and what he does to rest, recharge and refocus his efforts. Listen, reflect and clarify what he says to you.
  • Ask permission: Ask if he is open to a different perspective and hearing your views. If he says yes, then share with him what your energy levels are like at the end of the workday and how you like to spend your downtime and recharge your energy levels. Ask if he is open to doing the daily debrief at either the end of the workday or at the start of the next workday.
  • Collaborate: Design what will work best for him and you about timing for the work debriefs. Be open to trying something new and seeing how it works for both of you. Indicate that you are open to making any adjustments, if necessary. Thank your boss for his openness and flexibility.

Keka DasGupta, corporate trainer, The Art of Life-ing, Toronto

The best way to create stricter boundaries that feel good for both you and your boss is to take a direct, honest communications approach that leads to supporting your shared objectives. In this case, that focus would be on how you can better strategize with him, and thus, be more successful together in securing new business from potential clients.

With this strategy, you can turn a potential “me versus you” dynamic into a positive conversation where you’re on the same side, looking at ways to improve the status quo together.

First, consider acknowledging the value of the debriefing process for both of you. Then, communicate how, while your boss may feel energized after such pitches, you feel like your energy is spent. Share how having some downtime after work is important for you, so you can give your all at work the next day.

Be proactive and bring some win-win solutions to this conversation, factoring in your boss’s working style too. For example, perhaps you can have a 15-minute re-group after a new business meeting is done, while the pitch is still fresh in both of your minds. Then, as a standard process, pre-book a follow-up meeting for the next morning to dive deeper.

A plan like this could take both of your needs into account and show your boss that you are committed to bringing your best self to the job, so you can build more business together.

Have a question for our experts? Send an email to with ‘Nine to Five’ in the subject line. Emails without the correct subject line may not be answered.

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