Four Questions These VCs Ask Before Every Tough Conversation

When you’re an investor, having difficult chats is just part of the job. These four VCs explain why they never just rip off the proverbial Band-Aid.

Four Questions These VCs Ask Before Every Tough Conversation
[Photo: julief514/iStock]

No one likes difficult conversations at work, but everyone has them eventually–some people more often than others. For venture capitalists, tough conversations come with the territory; their jobs require them to tell founders they aren’t cutting it, that they’re getting removed from their companies, or that it’s time to close down their startups and halt their dreams.


Here are a few questions that several VCs say they ask themselves before going into a discussion that’s likely to leave somebody disappointed, frustrated, or worse.

1. What Might Go Wrong If I Don’t Say Anything?

It’s normal to want to avoid having to deliver a painful message, but Catherine Ulrich, managing director at FirstMark Capital, prefers to flip that negative–and make it unbearable to not share the tough news: “For example, when meeting with a company, if I don’t share the risks I see, then I am not giving them a change to respond, and I am also not giving them the best chance of success,” Ulrich points out.

This can come in handy for managers, too. Whenever you’re nervous about hurting feelings, consider the damage you might be doing (or the responsibilities you’re shirking) by not speaking up. “If I don’t tell an employee the areas where they are falling short,” Ulrich says, “then I am not giving them an opportunity to improve, keep their job, and grow as an individual.”

2. Have I Communicated Clearly Enough?

“The key thing we all have to ask ourselves going into any sort of difficult conversation is whether expectations have been clearly communicated–and whether past failures to achieve expectations have been properly called out,” says Will Porteous, general partner of RRE Ventures.

So before every tough chat, Porteous makes a point not only just to review the expectations he’s already imparted, but also to ask whether they actually got through to people and consider which new expectations might need to be set going forward. “Some of us are more self-aware than others. Some of us are more reluctant to acknowledge our shortcomings,” he acknowledges. “And so this is where the record of expectations and past communication comes up.”


“Being a good manager, boss, or founder really hinges on doing those two things well,” he continues. “I find that the more informal and collegial the work environment, the more people struggle to call out their direct reports on failing to achieve expectations.” The solution isn’t necessarily a more formal work culture, just clearer communication.

3. Will This Get Worse If I Wait?

Philip Sanderson, investor at Ridge VC, has seen a pattern among the 50 or so startups he’s worked with. It’s “when the CEO gives employees with performance issues ‘too much rope,'” he says. By shortening the rope, Sanderson doesn’t necessarily mean imposing more oversight (although that might be part of it), just jumping in earlier.

This is likely to be an uncomfortable discussion, so to get himself ready, Sanderson tries to remind himself of the perils of procrastinating. “The key is to have the difficult conversation with, say, the VP of sales as soon as possible,” he explains. “Put them on a plan and offer the ability to show they can perform with realistic milestones. Coach them closely.”

However, Sanderson believes it’s important to maintain that sense of haste even after the hard chat. “If they don’t step up after four to eight weeks, make a change fast,” he counsels. “Too many CEOs don’t have that conversation early, and it leads to holding onto a non-performing key employee an extra quarter or two–which nobody can afford.”

4. Who Haven’t I Heard From Yet?

“When times get difficult, teams benefit from transparency about how things are going,” says Brian Laung Aoaeh, investor at KEC Ventures. Communicating about those struggles, he believes, “should be configured to be both top-down and bottom-up in order to yield the best results.” Before breaking tough news, Aoaeh says leaders need to immerse themselves in their organizations and ask for feedback. The reason is simple: “Team members who feel heard are more likely to give their full support to the group’s final decision, even if it is one they disagree with.”

As Aoaeh puts it, “A culture of communication makes it easier to have difficult conversations–when they become necessary–than a culture of silence and secrecy.” This can reduce some of the fallout from a tough conversation as well, since more information means a greater likelihood that everyone can foresee what’s coming–including the not-so-good stuff–and respond to it proactively. “As it turns out,” adds Aoaeh, “extreme communication generally enables extreme accountability.”

About the author

Beck Bamberger founded BAM Communications in 2008 and writes regularly for Forbes, Inc., and HuffPost about entrepreneurship, public relations, and culture.