Leadership Essentials

⏱ 9 min read

In a rush? Here is the quick overview.

The issue

• Salespeople spend their days bouncing between prospecting, selling, negotiating, problem-solving, and handling rejection. Without consistent leadership touchpoints, they can easily lose focus, confidence, or momentum.
• Most leaders cover some of the important touchpoints, but missing even one can leave reps without the well-rounded support they need.

Best practices for you as the leader

• Create a consistent cadence for goal planning, pipeline review, coaching, and one-on-one meetings.
• Use each touchpoint for its intended purpose so your reps get tactical clarity, deal support, skill development, and relationship-building time.
• Stay flexible when meetings overlap, but review your cadence regularly so no touchpoint quietly disappears.

Key takeaway

Strong sales leadership is not built through random check-ins. It is built through consistent, intentional touchpoints that help reps stay focused, supported, and growing.

The Problem at Hand

Being a sales professional is not for the faint of heart.

One minute your rep is hearing “no” after “no” after “no” during prospecting. Then suddenly, someone is interested, and they have to jump into excited, consultative selling mode. A few minutes later, an upset client calls, and they are suddenly in customer service, problem-solving, and negotiation mode.

Tactically, salespeople pivot all day long.

• Sales.
• Admin.
• Sales again.
• Customer Service.
• Back to sales.

Emotionally, it can be a roller coaster.

• There are the incredible highs that come from closing a deal they have worked for days, weeks, or months to win.
• There are the rock-bottom lows when a deal falls apart unexpectedly.
• There is anxiety when their numbers are down and they need to get them back up.
• And honestly? There is anxiety when their numbers are up, too, because now they need to keep them there.

Sales leader, I am not telling you anything you do not already know.

But I do want to talk about two things your reps need from you.

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Consistency and Targeted Support.

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Consistency matters because sales already has enough emotional swings. Your reps need to know that you are steady, reliable, and paying attention.

Targeted Support matters because generic leadership will only get you so far. Your reps need specific guidance that helps them build skill, confidence, and momentum.

Here's the best way to ensure you are providing both.

The LeDev Advice

The Four Touchpoints Every Salesperson Needs

In my sales leadership career, I found that there are four major touchpoints every sales leader should have with their reps on a regular basis.

Most leaders do one or two of these well.

Some do three.

But when one is missing, the rep does not get the well-rounded support they need to be their best.

You may call these meetings something different in your organization, and that is perfectly fine. The names matter less than the purpose. What matters is that each touchpoint has a clear intent and a clear value.

Also, your team size will affect how often and how deeply you can do each one. If you have eight or fewer direct salespeople, you should be able to manage these consistently. If you have more than eight, you may need to shorten them or adjust the cadence.

But I would not recommend cutting any of them out completely because each one serves a different purpose.

All right, here we go—the FOUR essential touchpoints of a leader.

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The Goal Planning Meeting

The What

Goal planning is a tactical review of the rep’s plan for the week. This is not a vague “how are things going?” conversation. It is a specific “what is your plan?” conversation.

The goal is to make sure your rep has a proactive, organized plan to build their pipeline and hit their goals.

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The When and Where

This usually happens weekly, either on Friday for the following week or on Monday before the week gets moving. Some leaders also do a lighter version daily, especially with newer reps or teams that need more structure.

It can be a short live meeting, or the rep can send you a written plan to review. Either way, this should not take forever. Ten to fifteen minutes is usually enough.

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The How

The conversation should cover things like:

• Who are they calling?
• What is their strategic focus for the week?
• What markets or accounts are they focused on?
• What resources are they using to prospect?
• What are their specific activity goals?

The vibe is: "Okay, what is your action plan to get the business flowing this week?"

For the rep, this creates focus.

For you, it gives visibility into whether they are being proactive, organized, and realistic about what needs to happen.

It is also a great opportunity to build confidence. A strong goal planning conversation should leave the rep feeling clear, energized, and ready to go.

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The Pipeline Review

The What

The pipeline review is where you look at the opportunities your rep is actively working and discuss how to move them forward.

The purpose of the pipeline review is not to interrogate your rep. It is to help them move business forward.

Let them talk through their strategy. Role-play with them. Brainstorm angles. Help them get unstuck. Look for skill gaps. Look for confidence gaps. Look for patterns.

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The When and Where

This one should be live.

Email will not do the job here because the value is in the conversation. You want to hear how the rep is thinking. You want to understand the quality of the opportunities. You want to challenge assumptions, brainstorm next steps, and help them see options they may be missing.

Typically, pipeline reviews happen weekly and should be on the same day each week. For most reps, thirty minutes is enough once you have a good cadence going.

If your reps have large pipelines, do not try to boil the ocean. Focus first on the opportunities closest to the money. On another week, step back and look at the pipeline by stage to spot patterns.

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The How

The leader and the rep review the pipeline together and brainstorm what's possible. Here's an example of a pipeline agenda:

• Leads reviewing your proposal or offer
• Where are they in the decision-making process?
• When is your next follow-up? What is your call plan?
• What are the chances they will accept?
• Leads you are actively talking to
• What is your plan to get them to the proposal stage?
• When is your next follow-up? What is your call plan?
• How serious are they? What are the chances you can close them?
• Leads you are prospecting
• How many of these are strong prospects?
• What is your plan to reach them?
• What does your talk-track sound like?

For the rep, it should feel like support that helps them close more business.

For you, this meeting gives a much clearer picture of what is actually possible in the coming days, weeks, or months.

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The Coaching Session

The What

The coaching session is where you observe the rep doing the job.

This might be a side-by-side, a call shadow, a ride-along, a review of recorded calls, or even a focused review of something specific, like voicemail messages or follow-up emails.

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The When and Where

Coaching sessions are usually done once or twice per month. Newer reps may need them more often, more tenured reps may need them less often—but they still need them!

And yes, your veterans will sometimes tell you they do not need coaching.

Do not believe them.

What elite athlete do you know who does not have a coach?

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The How

First, spend time observing your rep doing the job. It can be a general observation session, or it can target something specific like observing cold calls.

At the end of the observation, give feedback.

• Start with what they did well.
• Choose one or two areas for improvement—max.
• Be specific.
• Give them tools or suggestions they can actually use.
• Send a recap so the conversation turns into action.

This is where coaching becomes personalized.

You are not guessing what they need. You are seeing it firsthand.

For the rep, this is where they get the kind of coaching that can make them meaningfully better.

For you, this gives real insight into skill gaps across your team. You may even notice patterns that should turn into broader training.

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The 1-on-1 Meeting

The What

The 1-on-1 is the most personal of the four touchpoints.

This is where you build the relationship, talk about engagement, discuss longer-term goals, and create space for the rep to bring up what is on their mind.

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The When and Where

These meetings usually happen monthly and last about an hour.

They should be live, private, and protected.

Because they are more personal, I'd recommend a more neutral setting like a meeting room or even an offsite location like a coffee bar.

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The How

The rep should have space to bring their own topics first. This is their time with you, and it should feel different from a pipeline review or tactical planning conversation.

You might talk about:

• How they are feeling about the role
• What is energizing or frustrating them
• Longer-term career goals
• Development opportunities
• Progress toward monthly, quarterly, or annual goals
• What support they need from you

You could also use this meeting (this is how I did it) to look at monthly, quarterly or yearly progress towards goals. How is their book of business doing against the long-term goals and what needs to be done to keep it going? Where do they want their numbers to be in the future? NOTE: if you don't fold this into your 1-on-1's you will need a separate monthly performance meeting.

I often used 1-on-1s to talk about both the person and the performance. Not in a heavy-handed way, but in a broader “where are you, where do you want to go, and how can I help?” kind of way.

For the rep, the 1-on-1 helps build trust. It gives your rep a chance to see the human, approachable side of you.

For you, it gives you a chance to understand what makes them tick, what motivates them, and what may be getting in their way.

And the better you know the person, the better you can lead the salesperson.

Putting it All Together

If this sounds like a lot, I get it.

It is a lot.

But it is also the work.

As a sales leader, your job is not just to react when numbers are off or jump in when someone is struggling. Your job is to create the structure, support, and rhythm that helps your reps perform consistently over time.

That does not mean every touchpoint has to be perfect.

Sometimes they will blend together.

You may walk into a pipeline review and realize your rep is emotionally distracted. That may need to become a 1-on-1 moment.

You may start a pipeline review and spot a clear skill gap. That may need to turn into coaching.

That is okay.

Be consistent, but do not be rigid.

The goal is not to check boxes. The goal is to make sure your reps are getting the right kind of support at the right time.

My pro tip: Keep track of the touchpoints you are having. At the end of each quarter, look back and see what may be missing. Are you doing plenty of pipeline reviews but very little coaching? Are you having good 1-on-1s but skipping goal planning? Are your newer reps getting enough structure? Are your veterans still being developed?

Adjust from there.

The Wrap-Up

If you are not doing these touchpoints regularly today, do not try to overhaul everything overnight.

Start small: Pick one and explain the change to your reps. Get consistent, then add the next one.

Try the cadence for a few months, ask for feedback, adjust, and keep going.

Summary