My teammate Banks and I were exploring what we’d say if a hypothetical genie showed up and offered us the ability to master any skill that could help our work most. After some deliberation, we both agreed: the ability to have hard conversations well.

We need to close the gap between expectations and reality. And that requires a hard conversation. Tweet This Quote

First, why do hard conversations matter? The reason is simple: things don’t go according to plan. We need more money than we thought to reach our next milestone. A new hire doesn’t work out. Schedules shift. In all these situations, we need to close the gap between expectations and reality. And that requires a hard conversation.

Second, what does it mean to have a hard conversation well? To me, it means delivering the truth respectfully and in a way people can understand. The truth is easy to deliver when news is good because we love making people happy. “Hey Ralph, you’re getting a raise!” Who wouldn’t want to say that to Ralph? The truth is hard to deliver when the news is bad because we don’t like causing ourselves or others pain, which is typically the consequence of bad news.

While pain is inevitable in having hard conversations, we can deliver the truth in a way that honors and respects another human being. Tweet This Quote

While pain is inevitable in having hard conversations, we can deliver the truth in a way that honors and respects another human being. The goal of this blog post is to investigate how to do that in ten situations that startup leaders often find themselves in.

1. How to fire someone.

This is perhaps the hardest conversation startup founders and managers have. The best article I’ve read on the subject is from First Round Review (by far my favorite blog series on startups), featuring the approach used by Michael Lopp, who “managed engineers at Apple for over eight years and now works at Palantir, where he focuses almost exclusively on maintaining and retaining some of the world’s best technical talent.” His main points of advice are:

  • Rule #1: It’s your fault. As CEO or manager, you most likely recruited this person, trained them (or didn’t train them), and didn’t lay out clear enough expectations. It’s on you to acknowledge this.
  • Tackle Performance Head On. If you believe that there’s a problem, don’t wait. Provide immediate, specific feedback, while taking the “threat” out of it, and have the employee in question repeat it back to you to make sure they understand.
  • Use a three-phase performance improvement plan, which consists of a degree of micromanaging for a month, providing only strategic counsel for the second month, and providing full autonomy in the third month.
  • Repeat offense—the tough conversation. Unfortunately, performance improvement plans fail at least 50 percent of the time, and when that happens, Lopp advises you to say, “We’re not doing this twice. It’s great that you can rise to the occasion when you need to, but we’re going to have to let you go.”
  • Crush Rumors with intentional communication to the rest of the company.

2. How to Let Other People Know You’ve Been Fired.

There’s little that I admire more than courageous honesty, taking responsibility, and finding a way to make the best out of a difficult situation. All three things are present in Andrew Mason’s remarkable and sincere letter to the employees of Groupon after he was fired as CEO. As Dave Checketts, founder and chairman SCP Worldwide, says, “Success builds character. Failure reveals it.” While this tactic might not be the kind that everyone who gets fired might employ, it’s the approach that I hope that I would follow if I were ever to be fired.

3. How to Give and Receive Feedback at Work.

Buffer, a company making social media sharing easier, is doing some extremely innovative things with their culture. They’re intentional about how they give and receive feedback, and Courtney Seiter goes into how they do this in-depth in this article. Some core elements include:

  • Reflect on your purpose [in giving feedback]
  • Focus on the behavior, not the person
  • Lead with questions
  • Inject positivity
  • Follow the Rosenberg method: Observations, feelings, needs, requests

4. How to Make Sense of Conflicting Advice from Mentors.

Mark Suster is one of my favorite startup bloggers. As a two-time entrepreneur and now venture capitalist, he brings remarkable insight to a variety of startup issues. His post on making sense of conflicting startup advice is no exception.

While dealing with conflicting advice isn’t a “hard conversation” per se, being able to do it effectively is important and ultimately leads to an ability to have hard conversations more easily. Board members, mentors, investors, and even teammates often get attached to their advice being followed, and if it’s not, you may have a tough conversation on your hands. Having solid justification for how you came to a decision you made, even if doesn’t align with what some of your advisors told you, is important. Mark’s advice consists of:

  • Triangulate: get multiple perspectives on big decisions.
  • Use frameworks to organize advice.
  • Thinking critically about your situation means comparing the context of the advice of advisors to the context of the decision you’re making.
  • Ultimately, go with your gut.

5. How to Cancel a Meeting.

This is not, obviously, the most difficult conversation that entrepreneurs have, however, it is an important one to execute thoughtfully. Mark Suster lays out how to cancel a meeting well in advance, the day before, the day of, and the hour of the meeting. He also talks about how to reschedule the meeting if there are multiple people involved and if it’s the third time you’re rescheduling.

6. How to Demote a Loyal Friend.

Some startup CEOs have to face the tough choice of bringing in someone more experienced to fill a role previously filled by a less experienced, but very hard-working friend. This can be an incredibly hard conversation to have and VC, Ben Horowitz, advises that you:

  • Be mindful of your friend’s possible feelings of embarrassment and betrayal.
  • Use appropriate language.
  • Admit reality.
  • Acknowledge the contributions.

7. How to Say No Gracefully.

Greg McKeown offers a humorous example from E.B. White on how to say no plus three principles for saying no, including:

  • Affirm the relationship.
  • Thank the person sincerely for the opportunity.
  • Decline firmly and politely.

In case you’re interested in another example, HubSpot co-founder Dharmesh Shah gives an example in this post, aptly titled “My heart says yes, but my schedule says no.”

8. How to Convince Investors.

Countless articles are written on this subject, but one of my favorites comes from Y-Combinator founder Paul Graham. The main requirement of convincing investors is “being formidable.” Graham explains that, “A formidable person is one who seems like they’ll get what they want, regardless of whatever obstacles are in your way.”

Convince investors only of what you already believe Tweet This Quote

So how can you be formidable? As Graham says, “You’ll never convince investors if you’re not convinced yourself. They’re far better at detecting bullshit than you are at producing it.” So, “the way to seem most formidable as an inexperienced founder is to stick to the truth,” and to convince investors only of what you already believe.

9. How to Apologize.

We all make mistakes and learning to take responsibility for them and apologize is critical to the health of startups. The main keys I outline in this post are:

  • Take 100% responsibility.
  • Be specific about what you’re apologizing for.
  • Acknowledge the impact of your actions.
  • Leave the words “if” and “but” out of your apology.
  • Make a commitment, even if it’s small.

10. How to Deliver Bad News.

We all have to do it, whether it’s telling investors we lost their money, telling our boards that we failed to hit our goals, or something else. Robert Bies gives the ten commandments for delivering bad news, including:

  • Thou shalt never surprise.
  • Thou shalt never delay.
  • Thou shalt never hide the facts.
  • Thou shalt always put it in writing.
  • Thou shalt always justify.
  • Thou shalt always look for the silver lining.
  • Thou shalt always bring solutions.
  • Thou shalt always remember your multiple audiences.
  • Thou shalt always follow up and follow through.
  • Thou shalt always treat people with respect and dignity.

There are innumerable other hard conversations we can all learn how to master. If you have any additional insights, frameworks, or examples of hard conversations, please share them in the comments below.

Teju Ravilochan

Author Teju Ravilochan

Teju is co-founder and CEO of Uncharted (formerly the Unreasonable Institute). He is driven by the desire to live in a world where every human being can be the master of their own fate, unbound by the chains of poverty, oppression, or injustice.

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