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  • Pivotal Advisors

3 Tips for Hiring and Managing a Sales Leader

Bringing in a sales leader (whether your first sales leader hire or replacing someone) is a big move.  This person is typically critical to driving the top-line revenue.  Hire a great leader and they can do great things to execute your growth strategy.  Hire poorly and they can do more damage than good -  not only hurting your top-line growth, but also disrupting your team and possibly even losing people.  This role is pivotal, so, it is important to get this decision right. 

Following are three tips to help increase your probability of getting a great leader:

Hire right

This sounds obvious, but companies mess this up all the time.  They typically hire someone with the following characteristics:

  • Come from the industry

  • Good track record of growing sales

  • Knows how to sell

  • Good at relationships – they are “people people”

  • Good at driving accountability

  • Honest/has drive/ethical/etc

Sounds like a good list, right?  I beg to differ.  Sure these are good traits but it doesn’t get at any specific skills.  You see, all sales leaders do not have the same skillset.  Some are better at being in the field, observing and coaching and developing the team while others are good at strategy and determining where growth will come from.  Some are good at building systems and processes to help the company scale (far fewer of these people) while most are good at running their system.  Some are good at hiring, building and structuring teams while others are good at managing the team you already have.  I could go on and on, but each of these things require different skills and experience.  Your first step in making this hire is to determine which set of skills you need.  Which are most important to executing your growth strategy.  Then, develop your interview questions around these specific skills.  Ask about their experience in whatever skills you’ve identified.  How did they learn it?  Give an example of how they’ve done it well in the past. 

Get really clear on expectations

This is an issue that we clean up a lot. Think about all the decisions that need to be made for this role.  Can they hire/fire?  Can they change budget?  Do they have purchasing authority?  Can they restructure the team?  These are just a few.  Can they do those things on their own or do you want to retain those decisions or can they do it, but ask first?  These may seem obvious, but there is often a chasm between the owner’s answers to these questions as well as the sales leader’s perception of that they can or can’t do.  Likewise, it is important to be clear on what you expect of them every week/month.  I constantly hear things from owners like “I wish my leader would spend more time in the field with their team” or “I wish they were more strategic” or something similar.  When I press them on how much time or what does being more strategic mean, I get two things back – 1) they can’t really define it well, and/or 2) they have not set that clear expectation with the sales leader.  Bottom line is that if you are not super clear about your expectations, they will never live up to them.  The best answer is to require your sales leader to present a plan to you on what they will do each quarter and for the year.  Get specific.  How will they go about getting new clients?  What will they do to retain and grow existing clients?  Where does the team need help and what will they do to develop them?   Make them present a specific plan to you inclusive of the metrics that you will watch together (both leading and lagging) to know if the leader is on track. 

Stay Aligned 

This is easier said than done. You get busy.  They get busy.  The result?  You don’t really have formal, structured one-on-ones.  Instead it is “What things do you have on your list? This is on my list.  Let’s talk.”  Or, more commonly, you have frequent, unstructured conversations (we call them fly bys) all the time, and you believe these are an adequate substitute for a good one-on-one.  Whether we do the “fly bys” or the unstructured one-on-ones, owners rarely get at the real meat.  Instead it is the issue of the day or deal of the day.  Do you want to stay super aligned with your leader? Then follow a one-on-one agenda similar to the following:

  1. What did you commit to last week?  Did you get those things done? 

    1. Yes? Good job.  

    2. No? Why? What do we need to do to make sure it gets done.

  2. How are you doing vs your plan? (See #2 above). 

    1. On target – all metrics look good.  Celebrate and recognize them for doing a good job.

    2. Not on target and/or metrics are off.  What are you as the sales leader doing to get back on track?

  3. What is the forecast?  Note: a pipeline is not a forecast.  We want to know what is real and we can count on it.  As part of that forecast:

    1. What are we very confident about?

    2. What is the upside or deals at risk?

    3. Based on those data points, what should WE forecast?

  4. How is the team doing?  Is anybody at risk?  Having issues?  Need reinforcement?   What are you as the sales leader doing to develop their skills?

  5. Issues you have?  Issues I want to discuss?

  6. Based on all of the above, what are your action items you are committing to for this week?

If you rinse and repeat this agenda each week, you stay aligned and you know the progress they are making.  

All of this may seem simple, but the execution often fails.  If you want to learn more or need help in this area, we would love to talk to you at


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