The CFO'S Perspective

Difficult Conversations at Work (and in Relationships)


As a finance team professional with years of experience navigating office politics, human relationships and life in general, I have the need to successfully complete difficult conversations every day. It is a skill that one acquires over time, especially after learning that it’s better to face problems head on.

It's easy to avoid the problems, bury your head in the sand, or pretend things are peachy, especially at work or in a new relationship. Avoidance only makes it worse for you and everyone around you - but mainly for you. When you go along because you're afraid of making it worse, you will slowly resent it and may leave your job or relationship because of it.

What if, instead, you faced these problems head-on, resulting in more positive working relationships and maybe even happier clients?

These problematic conversations take many forms – they could include

  • Your coworker/peer tries to delegate all the hard work to you.
  • You get passed over for promotion, or your bonus was less than expected.
  • The person you are dating is not treating you how you expect and deserve.

How to have these difficult conversations

  1. Difficult conversations are not effective via email or text

Do not even try to have this conversation via email or text! These conversations need to be in-person or via video meetup or, if either is unavailable, then a good old phone call. Make sure you allow enough time and set the expectation that this will not be a one-and-done meeting. You will have follow-up meeting(s) to check on progress towards solving the problem.

  1. Prepare but don't obsess

You don't want to wing it. It would be best if you wrote down what you want to say.   Document specifics that support your request – this includes specific dates, events, and what happened from your perspective. Be as specific as you can. Practice saying it out loud – use your trusted friends to rehearse. This will significantly help you get feedback on how you come across.   Keeping it in the "I" perspective would be best, not blaming the other person.

  1. Rules of engagement

After you tell the person what you want to say,

>  Stop talking and let them respond.
>  Listen to what they have to say.
>  Pay attention.
>  Let them talk and hear them out.
>  Ask for clarification if you don't understand something they are saying. 
>  Be prepared for the outcome.

  1. Examples of how to say it

EXAMPLE 1 - You feel your coworker delegates work to you.

You might say, "There is something I need to discuss related to you and I working together. Even though we are peers in our roles, I have recently noticed that you have been delegating administrative work to me regarding our clients over the past two months. And you do this via email, emailing the client and copying me, saying I will follow up and complete the administrative items.

My understanding when I started was that we share these responsibilities. Here are specific recent instances this has occurred.  

- instance 1
- instance 2

Are you willing to discuss this so we can work out an amicable solution?   I would like to hear your thoughts."

EXAMPLE 2 - The person you are dating is not treating you how you expect.

You might say, "This is the second time you have canceled a date, which concerns me. I would like to know if I should be aware of something. Canceling at the last minute is not the type of behavior I expect to experience in a close relationship."

EXAMPLE 3 - You have noticed a different behavior, such as a peer, associate, or close personal friend giving you the silent treatment.

Say something like, "I have noticed that sometimes when I disagree with you, you clam up and seem angry. I am curious about that reaction."

Your inquiry allows them to be honest and helps them gain self-awareness about their behavior.

  1.  You only have to be brave for 10 seconds

The hardest part is being brave enough to "say it."   Once it's said, you can move on to coming up with the next steps and agreeing on a solution.  

  1. Make a decision

Set a timeframe to check-in. Maybe it's two weeks, one month, etc. These follow-up conversations will be easier and hopefully productive. If nothing changes, you have to decide on escalating it or moving into a different role, company, or relationship, depending on the problem you're experiencing.

If your coworker's behavior doesn't change, you need to escalate to your boss and HR. Hopefully, they can help

If the person you are dating reacts negatively to your calling out their behavior, you might say, "I expect the person I date to be willing to engage in healthy, open conversations." If they cannot open up and tell you more, you will need to decide if you want to pursue the relationship.

Difficult conversations are certainly not limited to peers or personal relationships. I find that in business development, preconceptions and world views vary wildly and definitions of terms become a barrier. “Did you mean ______?” is a question asked frequently.

Tough conversations happen daily and can be awkward and unpleasant. "Fight or flight" response might kick in, resulting in an instant "avoid or attack" response. The key is to approach them with honesty and empathy. With an intentional, proactive plan for conversations full of potential conflict, you create a win/win relationships. Too many times the other person is unaware of issues and their world view has them believing all is well.

What I shared with you today has worked well for myself and others. With these tips, you should be able to successfully navigate difficult conversations while growing your potential. Of all the tips, #5 stands out. Taking action with a listening ear and open mind clears the way for new paradigms.

About the Author

Jen-GirardAt CFO Selections, Jen Girard’s role is focused on helping businesses succeed and grow by matching each company’s unique financial needs with the right resource and solutions.   

Jen has more than 25 years of professional services experience focused primarily in consulting, client service, engagement management, and talent acquisition. She has served clients ranging from startups to those in extensive growth stages, and those experiencing M&A transactions. Her industry focus has included technology, real estate, construction, transportation, manufacturing, and distribution.  
Learn more about Jen here >

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