Retaining Your Talent

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🔗 Jake’s Picks

Must-Read Resources for Founders

🚀 Scaling Startups

• From start-up to centaur: Leadership lessons on scaling (McKinsey & Company)

🧠 Founder Self-Development & Mental Health

• Lessons from a startup founder at the crossroads of failure (Fortune)

📈 Productivity Hacks

• Stop trying so hard to be productive and start ‘settling’ (CNBC)

🛠 Tools for Scaling

• Best customer feedback tool of 2024 (Techradar)

💡 Hiring Insights

• 5 tips for switching to skills-based hiring (CIO)

👀 ICYMI

• Recruit with AI (Scale Smarter Newsletter)

🎨 The fine art of retaining talent

Building and maintaining a team that grows with you is the foundation for any great company that scales.

On paper it’s simple—you want to scale your company?  Hire great people who can make it happen.  In reality, it’s one of the toughest things to (continuously) do - not only hiring great people, but creating a space where they want to stay, hopefully for a long time.

Typically when employees stay longer, they become more valuable to your company, both with their deep understanding of how the company works and their eventual ability to pass knowledge on to others.

There are of course (Hollywood) exceptions to this:

Employees who are in it for the long run become the knowledge continuity your company needs to scale.

They also become the backbone of the company as the time they spent learning your processes and systems makes them the most efficient workers, increasing productivity and lowering your costs knowing you don’t have to deal with turn over and hire for their position.

But in order to create loyal employees, you need to set up an environment that is conducive to them wanting to stay around.

Contributions that are noticed and rewarded

It can be as simple as a thank you.

Who doesn’t want to feel valued and appreciated for their work? Recognize and celebrate your employees’ accomplishments and watch what it does to morale and their commitment to the company.

Encourage growth, professionally and personally

Employees want to feel like their company wants to see them succeed, not only within their career but also within their life in general.

Creating an environment where employees can level themselves up builds another relationship layer between your employees and the company, strengthening their desire to stick around for the long run.

Let your people lead

You’ve hired your employees to take the company to new heights, let them take the reins.  Allow your people to lead when it makes sense and create an environment that allows for their creativity to shine through.  They’ll thank you later.

🏛 The four tactical pillars of retention

Alongside creating a comfortable and happy environment for your employees, as a leader, there are key tactics and strategies you can do, putting your company in the best possible position to retain employees without the heavy lift.

Weekly retro meetings

This was by far my favorite meeting when I managed teams at Uber.  Every week they were structured as follows:

1. What went well this week?

2. What didn’t go well?

3. What will we do differently in the future?

As a result, these meetings...

• Encouraged the team to share what they were working on

• Brought up things that were broken or just not working

• Created a forum for the team where they could be heard in a group setting, scaling communication in a one to many setting

Team members not only learned amongst themselves, but as a leader, it gave me the opportunity to address the things that weren’t working and work as a collective to fix them, which scaled nicely.

Gap analysis for your employees

Define these three things with your employees:

1. Where are you currently at?

2. Where do you want to be?

3. What are the gaps that need to be filled to get you where you want to be.

With these points clearly defined, your employees will feel much more confident in what they need to do to level themselves up, and with that newfound confidence, they should feel like there is a greater purpose in remaining with your company.

Defining the “North Star”

Much like conducting a gap analysis, clearly defining what an employee's goals and achievements are is key to understanding the steps they need to take within the company to reach their full potential.

When employees create a clear sense of what their North Star is and how to reach it, they become tied to this greater sense of striving for achievement, which ultimately leads to positive retainment outcomes.

Transparency with your team

Share what is going on with the company as much as possible. People generally want to know if what they’re doing matters or not and the more you can share, the easier it becomes to tie their contributions back to the overall mission of the company.

I used to share P&L metrics with my team all the time.  When my employees knew that the line items in the financials were directly impacted by the great work they did, they immediately saw their purpose and how they personally affected the company’s overall goals.

Strong employee retention is often driven by intrinsic motivations: autonomy, mastery, and purpose.

When you provide employees with the tools and freedom to excel, opportunities to advance their skills and share knowledge with peers, and an environment where they can see the impact of their work, you create a self-sustaining culture of retention.

🎬 TLDR — Your Actions For The Week:

• Scale Your Team → Look to an employee to be a peer coach that supports other employees

• Scale Yourself → Try a gap analysis meeting with your employees to set up their self-growth journey

Whenever you're ready, here’s how I can help:

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