The Startup Help Desk podcast

How to handle Underperforming Employees

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In this episode we answer questions about underperforming employees. If you have a team, some people on that team will underperform. What do you do when that happens? Can you turn them around, or do you have to let them go? We are here to help! In this episode we answer questions including:

  • How long should you give an employee to ramp up?
  • Why would a top sales person start missing targets?
  • What do you do about executives that aren't working full time?

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Your hosts:

  • Sean Byrnes: General Partner, Near Horizon www.nearhorizon.vc
  • Ash Rust: Managing Partner, Sterling Road www.sterlingroad.com
  • Nic Meliones: CEO, Navi www.heynavi.com


Reminder: this is not legal advice or investment advice.

Q1: How long should you give an employee to ramp up?

An underperforming new hire is not good news. You should be excited about new people joining your company, not concerned!

It is critical to move quickly. For a technical new hire, you want them to at least be pushing code by the 2 week mark. If a new hire hasn’t made you say “wow” in the first 6 weeks, the odds of it working out are not in your favor.

Overall, an 8-12 week ramp up timeline is reasonable, as long as you are seeing the proper early milestones and an acceleration of key contributions. That being said, if it is not working out by as early as the 2 week mark, you need to take action. Remember, the longer you keep someone who isn’t working out, the harder it is for them to explain the gap in their resume. Thus, deciding to part ways early in the process can benefit both your startup and the new hire.

Q2: Why would a top sales person start missing targets?

Start by investigating why they missed their targets. Is there not enough pipeline? Are their close rates low? Figure out if it’s the sales person, the pitch, the process, or another factor.

Interact with the sales person regularly to correct course. Always make sure you are setting clear expectations. Get them a coach. Pair them up with someone doing well. In short, do what you can to intervene, understand the issue, provide support, and get back on the winning path.

Top sales people are in high demand. If it turns out the performance issue is a result of them interviewing elsewhere, evaluate your incentives plan to see if you are creating enough reasons for them to want to stay and keep performing at a high level.

Q3: What do you do about executives that aren't working full time?

First, have a serious conversation about expectations around availability. Second, focus on why people want to stay. Give them reasons to want to work hard! Finally, make sure motivation and engagement is part of your interview process. Hiring motivated self-starters is always in season.

Ultimately, you want underperforming executives to turn the tide and start creating more value for the company. Consider setting more ambitious goals for them. In doing so, you will have a measurable way to see if their output rises to the occasion which, in turn, should result in increasing their work-time presence. Include regular check-ins as part of the process to achieve the goal.



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