Crucial Skills®

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Crucial Conversations for Accountability

How to Tell Your Employee Their Expense Won’t Be Covered

Dear Crucial Skills,

My assistant used $700 for a hotel room. I had never given him a spending limit, but I didn’t think he would spend $700. Now I need to tell him he won’t get reimbursed for that because it was way too much. How do I tell him? Help!

Pretzeled Purse String

Dear Pretzeled,

I’ll start with the bad news. I can’t help you tell him he won’t be reimbursed because that is the wrong conversation to have. From where I am sitting and what you have shared, you need to reimburse him and then have the conversation about appropriate travel expenses going forward. Admittedly, that probably means the tough conversation you will be having is with your boss, when you explain you need to find the budget to cover this hotel expense because you didn’t set expectations up front.

That’s the bad news. The good news is, every time an expectation is missed, we have an opportunity to clarify and re-set expectations going forward. A missed expectation is a chance to do things differently going forward. So, let’s unpack the situation.

First, you didn’t set clear expectations up front. You made some assumptions about “appropriate” behavior based on your paradigm. That is on you, and you need to take responsibility for that. Learn from this that you should have a clear travel policy that you share with new employees up front. Do this for yourself, and for them. No new employee wants to make a mistake right out of the gate. When we as leaders fail to set clear expectations, we set our employees up to fail. That’s not fair to them.

Next, use this opportunity to clarify how you want to work together going forward (when it comes to travel or any other expectation). This is a critical time to demonstrate to your employee how you will handle a situation when something goes awry. Show up well here and you will be laying the foundation for a positive, collaborative, accountable working relationship going forward.

To do this, start by sharing your good intent. Why are you having this conversation? And more importantly, what do you want for this person coming out of the conversation? Too often we go into accountability conversations like these with a clear idea of what we want for us… but not for the other person. In this case, sharing your good intent might sound like:

“I want to chat with you about your recent travel expenses. My goal is to make sure you and I are aligned and that you are set up to be successful going forward.”

Then, describe the gap between what you were expecting and what you have observed:

“I noticed you spent $700 on your hotel room. I realize we didn’t discuss this beforehand, but that is a lot more than our employees typically spend and I was surprised by the amount.”

Again, make sure you own your part in this—that you didn’t give guidelines up front.

Finally, set a clear expectation for going forward:

“I’ll send you our employee travel policy today so you have a clear understanding of the guidelines.”

Conversations about expectations become much easier when you see them as collaborative rather than directive. “My job is not to hold you accountable. Instead, our job is to work together to understand and close the gap between what was expected and what really happened.” When we become part of the conversation, we are able to look at and take responsibility for how our action (or inaction) has contributed to the gap.


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7 thoughts on “How to Tell Your Employee Their Expense Won’t Be Covered”

  1. Carol Olsen

    I understand your response to the high spender, however, I think I would begin the conversation in a different way. I would attempt to understand their behavior by asking them what they assume or think about when traveling on an expense account. In other words, understand more about the reasoning of the spender before the rest of the conversation takes place.

  2. Erin Rauser

    As someone who books travel for my company, it’s also worth checking the market the employee was staying in. There are many places with very high room rates. Hotels in the same market with lower rates may have poor (and possibly unsafe) conditions.

  3. Linabelle Wentworth

    Love the accountability placement here… many times we resort into holding accountable the wrong person. Yes, we all expect common sense used when booking travels, but setting the expectation is always on the manager. What if the employee comes from another organization that was more deliberate in spending their money on luxury because that is what their culture was? This is not on the associate if we don’t clarify what is our policy.

  4. Robert Arends

    One element that may be missing here is adding a level of curiosity and asking what made the bill total reach $700.00. There might be legitimate reasons for it.

  5. Melanie Gao

    This is a great reminder to reflect on the question – which conversation do I need to hold? It’s easy to focus on how to have the conversation, but that’s no use if we’re not holding the right conversation in the first place. So wise, as always, thank you Emily!

  6. Adina B

    I also wanted to chime in to say that on some particular days, hotel room rates are incredibly inflated! One time, my work travel partially overlapped with a music festival in that particular city, and that hotel night was >$600! Very average hotel experience, but 3x the price! Do make sure to give the employee the benefit of the doubt, and maybe you’ll find that reimbursing the $700 is actually very much appropriate by anyone’s standards, with the added information in mind.

  7. AnonaMouse

    Had a previous boss who totally and completely botched almost this exact conversation. We asked for approval for 3 choices of restaurants to celebrate a gentleman who had contributed a lot to our department and was moving on and being promoted to another department within the company. My boss said to just go to any of them, enjoy, and send him the receipt when you are done. We went out to a nice steakhouse (approved by my boss) and between the 5 of us, spent (excluding tip) $275. We encouraged the gentleman who was leaving our department to get whatever he wanted – $100+ plate – and the remainder of us stuck to the lunch menu < $50 / plate. My boss never set clear expectations and when I turned in the receipt, he called me "wildly irresponsible" and refused to reimburse me. It was the straw that broke the camels back and I turned in my resignation shortly thereafter.

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