Tell me about a time when you handled a difficult stakeholder.

Purpose of the Question

Questions like these get at two key skill sets:

• Ability to work with others who have different styles and/or interests.
• Communication skills to discuss contentious situations collaboratively.

Your answer should demonstrate how you uncovered the source of disagreement between you and a stakeholder and a level of adaptability to change your approach to bridge that difference.

Preparing to Answer

Questions on conflict generally take one of two forms:

• “Tell me about a time when you worked with a challenging stakeholder” - this variation focuses more on a specific stakeholder and how you built a working relationship with them.
• “Tell me about a conflict that you navigated” - this variation is asking more about a situation, but really strong answers typically feature some stakeholder at the other end.

We'll work through the first case as an example.

First, choose an example. When assessing which scenario to use (ideally pre-prepped with the help of your story bank!) consider the following:

• How great of a deal was it to resolve this conflict? Don’t be fooled by a relationship-oriented question -- you need to cover the business impact of your work. This could be measured in revenue / metric impact, organizational efficiency, or some other form of measurement that mattered to the team.
• How proactive and insightful were you in the discovery process of the conflict? The interviewer is looking for a clear story of how you uniquely bridged an interpersonal gap, so that part of the story should be robust.

Next, tell the discovery story. Within the typical STAR method of delivering interview answers, make sure you build out the discovery component of your actions. How did you first identify the conflict / difference as a problem? What approach did you use to understand the source of that difference? How did you use that information to bridge that gap? Don’t be afraid to go into details around the conversations you have with other teammates or your thought process at different points in the story.

Remember, don't take disagreements personally. Because BizOps often operates in contentious situations, tough conversations are unavoidable. Teams highly value the ability to debate and disagree in one situation but still maintain constructive partnership in another. That’s why it’s extremely important to characterize these conflicts or disagreements carefully around a specific area rather than the person holistically.

Example Answer

Interviewer: Tell me about a time when you worked with a challenging stakeholder.

That’s a great question! Hmm, the situation that comes to mind is a time when I was building the business case for a marketing investment but experienced pushback from our sales team. Does that sound interesting to you?

Give your interviewer the opportunity to provide explicit feedback on whether this is the type of answer they’re looking for.

Interviewer: That sounds great.

Historically, we’ve grown the business through B2B sales, so marketing is a pretty underutilized channel. I was building the marketing investment case to expand the company’s spend in paid marketing, but as I built out scenarios for the revenue impact we think the marketing spend can bring in, one sales leader, I’ll call him John, kept casting doubt on that forecast.

Naming the characters in your story can be helpful for referring back to them.

I was confused by this resistance because he’s always been a reasonable stakeholder to partner with, so I started digging in.

Clarify that the stakeholder challenge is situational, not inherent in your relationship with that person.

I set up a one-on-one meeting with John to better understand his perspective. In that conversation, he shared that he didn’t believe in how the marketing team measured its impact right now. Digging into that point further, I realized that the marketing and sales teams operated in relative silos both in terms of strategy and measurement, which is a huge problem for enabling both teams to operate effectively.

The most powerful stories uncover a bigger issue from smaller interpersonal situations. In this case, John being a difficult stakeholder is a symptom of broader misalignment within the organization.

With that insight, I kicked off two workstreams. First, I expanded the scope of the marketing investment business case to explicitly address how it connects to the sales team’s strategy. This perspective helped the marketing team update its prioritization. Second, I enlisted a data scientist to help build a more robust reporting infrastructure or marketing, so that we can track marketing-converted customers’ performance within the sales organization.

It’s always a good practice to number the list if there are several actions or factors in play.

With this reformed approach and greater impact visibility, John agreed to allow the investment case to go through. The investment case ultimately allowed us to spend $8M marketing budget to bring in $40M annually, enabling the business to grow 2%ppts faster.

Close with quantitative results - remember, don't neglect business impact!