Lenny’s Newsletter · Free post · Leadership & management · Communication & influence

This Week #7: Effectively communicating about a failure to execs, managing founder expectations, and hiring a Director of PM

### Q: What are your thoughts on communicating failure, like missing our team’s set goals?

Lenny RachitskyOct 29, 201910 min♥ 75
SourceLenny’s Newsletter
KindFree post
PublishedOct 29, 2019
Readers♥ 75
Originallennysnewsletter.com ↗
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This weekly Q&A from Lenny Rachitsky covers three reader questions: how to communicate a failed MVP to leadership, how a product manager can persuade a founder to change a core idea under board pressure, and what to look for when hiring a Director of Product Management. The failure advice reframes failure as normal and urges candor, a clear plan for next steps, and ownership. The founder advice favors shared journeys, cheap hypothesis tests, and letting the founder save face. The hiring section contrasts director roles with IC PM roles and offers interview prompts across strategy, people leadership, stakeholder management, impact, communication, decision making, vision, and hiring. The advice is practical and stays relevant beyond its 2019 date.

01Key takeaways

  • Be upfront about failure and frame it with what was learned and what the company should do next.
  • Spend most of your preparation time on a clear recommendation for next steps after a failed launch.
  • Change a founder's mind through shared discovery, cheap hypothesis tests, and data they cannot easily dismiss.
  • Give leaders a face-saving narrative that treats a pivot as evolution based on new information.
  • Recognize when a founder is unlikely to change course and decide whether to stay in that environment.
  • When hiring directors, test long-term strategy, people leadership, and communication through concrete past examples.

02Key sections

Reframing failure
Failure is common in new projects and should not be equated with personal failure. Keeping the stakes in perspective helps the presenter stay calm.
Presenting bad news to leaders
Be upfront, stay positive, separate idea quality from execution quality, and walk through the project's journey and learnings. Close with a clear recommendation for next steps and show continued commitment.
Changing a founder's mind
Bring the founder along the same learning path, align on key hypotheses and test them cheaply, and present compelling data. Enlist trusted advisors and give the founder a face-saving way to evolve the plan.
Hiring a Director of PM
Director candidates differ from IC PMs by managing PMs, owning large scope, and working with senior leaders. Interviews should probe strategy, people leadership, stakeholder management, impact, communication, decision making, vision, and hiring.
Interview question examples
Sample prompts ask candidates to walk through a long project, handle low performers, disagree with managers, communicate delays, and explain their decision-making and measurable impact.

03From the post

“Hello and welcome to my humble newsletter, where I attempt to answer your questions and offer candid advice about building product, driving growth, working with other humans, and anything else that’s stressing you out at the office. 🤝 If you’re returning from last week, thank you! If you’re new, nice to have you! Help spread the word by telling your friends to sign up here. 🙏 New this week:A friendly reminder to click the little grey heart up near the headline, if you find this newsletter valuable. <3 On to this week’s questions… [](https://substackcdn.com/image/fetch/$s!EgGv!,fauto,qauto:good,flprogressive:steep/https%3A%2F%2Fbucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com%2Fpublic%2Fimages%2F6253a3db-f579-46f5-8820-2f6430f63697220x118.gif) Q: What are your thoughts on communicating failure, like missing our team’s set goals? I’m new to my job and the first idea I pitched got buy-in very quickly. However, even through the initial user tests went great — the actual MVP we launched is doing horribly. I am struggling on how to communicate this, and which actions to take. Unfortunately I am in a quite “old-fashioned” environment where sharing failure is not common. Before getting into how to deliver bad news, a few suggestions to…”

“Leaders respect people who are clear-headed, up-front, and take responsibility.”Lenny Rachitsky · Lenny’s Newsletter
“Share them as you experience them, with your takeaways, and always with a "here's what we're doing next to continue learning how to make it…”Lenny Rachitsky · Lenny’s Newsletter
“Bring them on the journey with you: It takes time to change someone's mind.”Lenny Rachitsky · Lenny’s Newsletter

04Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.