Why You Should Always Be Training Your Replacement

Photo by Jesse Orrico via Unsplash

If you are the Top Sales Rep, a Team Lead, a Manager, a Director, or a VP, you should always be grooming someone to replace you.

Many leaders neglect to do this. When they do, they are dooming themselves and their teams to complacency and mediocrity.

There are many good reasons for training your replacement:

  • If you want to be promoted into a new role, having someone ready to step into your role to provide a seamless transition for the company is critical.
  • As a leader and a mentor, you developing your All Star employee’s skills while helping him to advance his career.
  • You transform from being a “doer” of the work to a leader who recruits, hires and develops others to do the work.
  • All Star employees need challenges and growth opportunities. If you let them stagnate in their role, they will leave you for a better opportunity.
  • You want to leave the team you cared about in the best hands possible. If, as a sales manager, you don’t feel this way about your team, I urge you to seriously consider a different line of work or else build a new team.


Here are some bad reasons why many managers have told me they don’t do this (and why I call BS on each one):

Fear of being replaced. Across 20 years when I have trained someone to replace me, it has never resulted in me losing my job. It simply didn’t happen. I always was offered better roles.

Loss of productivity. Of course I can do my job better than anyone on my team. When I take the time to teach someone else how to do my job, it will take much longer to get the same work completed and they won’t deliver the high quality that I do – initially.

But as a sales leader, it’s my job to exponentially increase my contributions to the company. If I train 2 people well, over time they’ll become fully productive and will deliver 200% of what I could.

In many cases, my replacement will become even better than I was. (For example, see my story about the Sergeant here. He went on to lead my old team to the #1 spot for years before building out several Sales teams of his own that dominated the industry.)

Fear of losing your best Sales Rep’s revenues. Guess what? You will lose his revenues anyway  when he leaves because he’s not being challenged or presented with growth opportunities.

Nobody on the team is capable (or interested).  That’s an issue that is your job to fix. Either recruit some All Stars or train your budding All Stars. Whenever I am hiring for my team, I am looking for future candidates to replace me and to backfill the top performers on my team. .

Fear that the employee will leave me for a better opportunity once he learned new skills. He might. I have had employees I groomed as my replacement leave to work for another manager or left for another company.

When that happens, it is still a good thing.

It’s a win for the employee who moves up.  It’s a win for my team, because a new spot opens up for others to fill. It’s a win for our culture, because tales of former employees moving on to bigger and better things foster a culture that attracts All Stars.

Below are some real life examples of what happened when I trained my replacement.

When I wanted to move up into my first Sales Job, my boss agreed to promote me into sales under the condition that I find, hire and train my replacement. I learned how to write a job description, screen resumes, interview, and train an employee from this experience. Because it took several weeks to get someone onboard, I also learned that the next time I wanted to move up, I should have a replacement in mind to backfill me.

When I was the #1 Field Rep for a fast growing startup and wanted to move into management I knew I had to first figure out a way to backfill myself so that our sales didn’t decline. Then I had to sell my boss on creating a management role for me.

I started by mentoring two of our junior Inside reps. I taught them how to do deeper discovery with B2B clients, how to design solutions, how to write proposals and how to move deals forward. I also started handing off some of my smaller opportunities to them to close.

In the short term, this meant I gave up commissions that I could have earned. But after 3 months, I was able to convince my VP to create a full-time management position for me because we could cover my “lost sales revenues” and grow even more if I built out the team. This worked – we grew annual sales from under $100K to over $25M over the next 3 years.

When I worked for a Fortune 1000 company, I was promoted to manage a sales team of 16 reps. I knew immediately that I couldn’t give my all of my reps the attention and coaching they needed.

There were two senior level reps on the team who expressed a desire to move into management and a willingness to take on extra responsibility to prove themselves.

Since this was a big corporation, I couldn’t just create official Team Lead positions because we had HR rules, budget approvals, and protocols to follow. To work around this, I started by making them “unofficial” Team Leads.

We created two teams of 3 Reps plus a Team Lead. Each Team Lead was responsible to provide day to day coaching on prospecting, pipeline management and closing for his team.

I had a weekly management meeting with my Team Leads. I solicited their input in management decisions, involved them in strategic work and had them lead team meetings. They loved it.

This worked out so well that my new team immediately turned around from being last on the floor to leading in quota attainment. I sold the idea to Senior Management over the next few months and within 6 months received budget to create official “Team Leads”.

Over the next 6 months, I assigned more responsibility to the leads, reduced their own individual contribution requirements and eventually phased out the Team Lead roles by replacing them with full manager roles.

What happened to me? Instead of coaching reps, listening to calls, and managing the team’s daily activities, I was able to get involved in more strategic initiatives and eventually was promoted to Director of Sales.

There have been occasions where it didn’t work out exactly the way I had planned:

At one startup, I groomed someone from Inside Rep  to Field Rep to Team Lead. We planned for him to replace me as manager so I could move into a Director of Sales role. Before that happened, our company launched  an Enterprise sales group and he was recruited into taking a role as the Sr. Enterprise Sales Rep. Being a fairly new manager at the time, I felt betrayed. It seemed like the 2 years I invested in him was all for nothing. I was seriously bummed out.

Now I had to not only find a new strong rep to make up for his sales and also start from scratch training someone else to backfill me.

Little did I know that this was going to work out well for everyone. I hired one of my all time best employees, the former pizza shop owner who became my top rep within 3 months and a team leader. My former mentee went on to have a stellar career in Enterprise Sales. As for me, I was still promoted to Director of Sales later that year.

Over the years, I’ve had several reps who initially expressed interest in management, but once they were given an opportunity to participate in management, decided it wasn’t what they had imagined. All of them went on to successful careers in individual contributor Sales roles. I’m pretty sure some made far more money with less aggravation than they would have had they stayed on the management track.

I’ve also had several of my All Stars leave my team to join other companies for better career opportunities than we could provide. I encourage my employees to do this. Many of them have become mentors for people on their own teams. In some cases we still keep in touch and occasionally help each other with recruiting, problem solving, referrals and brainstorming.

I’ve only had one truly negative experience. I was so impressed with an entry level administrator we worked with that I offered to create a leadership role on my team for her. She was thrilled. We spent several months training her for the new position and driving sales so we could fund the role. When I got the role approved, we agreed on the salary and set a start date. At the last minute she rejected the position and left the company to take a position at one of our vendors.

I took her leaving as a personal insult. My mentor counseled me, “Forget her and focus on finding someone else who is capable of doing this job. You created a great role that we need to fill and you’ll find someone to do it.”  He was right. We did. And until I wrote this post more than 15 years later, I did forget her.

That’s a wrap. You know what you need to do.

Happy Selling.

If you want some help building your sales team or improving sales, contact me here. I’d love to hear from you.

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