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Midnight Text: How Do I Lead An Engineering Team?

Alexis Clarfield-Henry
Apr 11, 2023
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min read

At Forum Ventures, we pride ourselves on really getting to know the founders we invest in, and creating (what sometimes is the only) space for them to drop their front and be vulnerable. As a result, we often get texts or calls in the middle of the night from our portfolio founders with urgent, confidential, and even sometimes what they feel are “embarrassing” questions. This series chronicles example founder texts and how we answer them.

First of all, an engineering team will never deliver fast enough for a founder. 

This is a common concern for founders. If you aren’t technical or an engineer by trade, you’ll never understand how long the work is supposed to take. 

If your team is delivering on a regular schedule, you should focus more on your patience than their progress. Unnecessary meddling and pushing will cause delays, and mistrust, not acceleration. 

But let’s assume something is going wrong: the team is consistently missing the deadlines they set. Then, you need to get to the root of it. It’s likely one of three scenarios.

1. People problems

Break the work down into who did what. Use this analysis to identify the delay spot and see if you can track it to one or two individuals.

If people delays are the case, here’s a rough process you can follow: 

  • Does the person have the key resources they need to do their job efficiently?
  • Does the person have the skills necessary for the task?

If they don’t have resources, it’s your job to provide them asap. If it’s about skills, think about the coaching vs. letting them go framework. Ideally, you can coach them up to speed (or get someone with a specialized skill set to teach them). However, if they can’t be brought up to speed fast enough (usually a matter of weeks), you need to either re-home them in the organization or let them go.

Also, what does your engineering leadership look like? Do you have an eng leader? If so, they can help decipher if/where there are issues. They should also be the one to coach the person who might be causing the delays. If you don’t yet have an eng leader, you should consider that role as your next key hire. 

2. Process issues 

A common process issue in startups is a founder asking for a delivery date before the engineering team has had a chance to fully scope. If your team continuously commits to a delivery date early on but never seems to hit it, take a look at who has been setting the deadlines. 

This is an easy fix: work with the engineering team (or CTO, depending on your structure) to reorient the process. Make sure the team can do all requirements gathering and scoping before making a delivery commitment. While this might mean a later delivery date than you’d like, it will be more accurate. 

Development processes like agile already have this built-in, if you need process inspiration.

3. Culture challenges

Perhaps the most sticky of problems is when your team feels they have to say yes to you, even if they know they can’t meet the demand. This is a sign that you’ve inadvertently created a culture of fear, and no one can thrive in that environment. 

If you want to solve this problem, you need to drop all pretenses and ask for pure honesty. And when you get it, you can’t get emotional, rude or unreasonable. You have to listen to their concerns, ask them to help co-create a solution, and ask them to commit to the solution as best they can. Create space to come back to you with ample notice if it’s going to take longer than they said. Remember systems are meant to grow and iterate over time, so you can’t hold them to the letter of the first idea they come up with.

I’ll end by saying that these kinds of challenges are fairly normal in a startup, so know that you’re not alone. And if you’re curious about leveling up your management and leadership skills, check out these courses and resources: 

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