Five Critical Skills A Sales Leader Needs

In recent months, I've done quite a few blogs on the specific, narrowly focused tactics that help to make sales leaders successful.  Today I want to take a different tack by focusing on what I believe to be the five most important skills a sales leader can develop over time to be successful in their role. They are listed and discussed below.

1. Be engaged.  This heads the list.  I can't tell you how many times I've talked to sales managers and their sales leaders and learned they haven't even spoken to their people in days or weeks. They say things like “I manage them through email.” Or: “I manage them through CRM.” Or: “I manage them through a spreadsheet.”  Or: “They know I am available if they need me.” That’s not leadership! You've got to be engaged on a personal level. When you're engaged, you talk voice-to-voice with your people on a regular basis. You know exactly what's going on in the pipeline.  You know where people are likely to be having problems.  You can see the trends occurring before they begin to have a major impact on someone’s performance. You know what to do, and you know how to coach the person, because you can see it all happening.  You're in it.  You hear it. As a result, you’re seen as a personal resource, as someone who offers value to the individual salesperson on a personal basis. 

I've reported to different types of sales leaders in my career.  The ones who just wanted to make sure I was in compliance, just wanted to make sure I had my reports done – I would give those people a D for leadership.  Then there were the ones who were really engaged with me on a personal level, the ones who helped me strategize calls and went on calls with me and knew the pulse of what was going on in my book of business, all of which increased my confidence. Those were the people I had the utmost respect for and worked that much harder for. I wanted to make sure that I met the expectations of those people. They get an A.

In today’s situation, I get that it's sometimes going to be difficult to earn an A for engagement. Everybody is remote.  We're all zoomed out. I understand that. But the fact remains: This is a core skill for leaders. We must be engaged in the business, and we must be engaged on a personal level with what’s happening in each salesperson’s world. 

2. Be inquisitive. Let’s face it. Taken as a group, sales leaders are not particularly curious. Why is this? Well, very often, we're pressed for time. When somebody brings up a problem, we may be tempted to just jump right to what we think is the solution. Have you ever heard these words from your spouse? “I don't need you to fix it, I just want you to listen.” There’s a lesson there for sales leaders. Of course we want to fix whatever the problem is. But to get to the right solution, and to empower the salesperson to solve the problem for themselves whenever that’s possible, we want to get better at two things: asking the right questions and listening with authentic interest to what comes back.

Most of us could get a little better at not assuming we already know what the salesperson is about to say or means to say. The truth is, we don’t always know what's going on within an account, and even if we do, simply solving the problem doesn’t give salespeople a lot of room to grow. So, we want to learn to ask better questions – including what I call assumptive questions. For instance: “When you asked the ultimate decision maker about X, Y, and Z, what did they say?” That type of question allows the sales rep to understand where the gaps are in their own sales process and empowers them to do a little bit of self-discovery, which is very important.  Remember: People don't argue with their own data.  When they reach their own conclusions, that matters more than us telling them what the right conclusion is.

The big issue when it comes to being genuinely curious is how interested you are in getting to understand your sales rep.  What is their thinking? What conclusions are they making? How are they getting from point A to point B to point C? Asking good questions from a position of genuine curiosity allows you to be a bit of a psychologist, which is a good role to play. You always want to get a better understanding of how they got to a particular point or reached a certain opinion.

3. Roleplaying.  Roleplaying has a bad rep among some salespeople, but if you call it modeling or practice, you can get over that prejudice fairly easily. Call it whatever you'd like, this skill builds confidence and conviction within your team.  Use it!

Roleplay what they’re supposed to do and say in specific situations. You will want to identify the top issues that salespeople are likely to run into in each of the separate stages of your sales process and you will want to make sure they have, and can deliver, a fluid, compelling talk track when the moment comes to discuss that issue with a buyer. Roleplay what they need to ask. Roleplay what you want them to qualify. Roleplay the process they can follow for getting good, clear commitments.

Why roleplay all of this? Because people need to hear what their mouth is saying. Without roleplay, what happens is they say, “Yeah, I know that, I understand that, I’ll do it that way.”
And they do believe what they are telling you. But when the moment of truth comes, and they’re supposed to say something out loud, it doesn't come out sounding anything like what they thought. They wing it. They fall short. And the only way to turn that around is through practice.

Roleplaying gives your salespeople the internal strength and the poise they need to execute at a high level of proficiency when it counts: in real time, during discussions with buyers. They don’t want to practice with buyers. (That’s why so many best practices never get implemented.) And be honest: You don’t want them practicing on buyers, either. You want them practicing on you.  

Your salespeople may not like roleplaying initially, but if you do it right, they will come to love it. I roleplay three to four times a day with our people.  It’s part of our culture. It’s always a positive experience. And it doesn't take a long time.  During one-on-one meetings, I’ll say “Well, how does that sound when you do it in a meeting?  Let me hear that.”  Or I’ll say: “Want me to take a shot at it?” I will actually model the best practice for them, whatever it happens to be, and then they will repeat it back.  That’s a great way to get salespeople into roleplaying: go first and show them how you want to see it done. Then let them have a turn. Who knew? It’s fun.

Roleplay does not have to be uncomfortable, and it does not have to be done in a public setting, but it does have to happen. Be prepared to jump into a roleplay at a moment’s notice, so you can give each member of your team the advice, the words, and the confidence to move forward.  Make role-play a daily reality for each member of your team!

4. Pre-call planning.  Pre-call planning is a critical sales leadership skill that involves leading a special type of planning conversation. This skill produces positive outcomes in two realms at the same time: yours as sales leader aiming to support a self-correcting team, and the salesperson’s as a revenue producer aiming to close a given deal.

This conversation establishes and reinforce all the things that you want your sales rep to do …

• in the sales process, as a matter of course, and
• on a particular sales call.

Pre-call planning is one of the very best ways to coach salespeople one-on-one. This conversation enables you to agree ahead of time about what's going to happen before the sales call even begins – as opposed to learning about what happened through your debriefing process. This conversation also allows you to identify potential skill and behavior gaps a given salesperson is experiencing. Last but certainly not least, this discussion lets the salesperson know what you are likely to ask about during the next one-on-one discussion, and thus inspires constructive action on the salesperson’s part while the two of you are not side-by-side.

I've got five children. I much prefer helping them study for a test prior to the event. That’s far better than learning, after the fact, that they failed their test.  In the first scenario, I can help because we’re talking before the event happens. In the second scenario I can only commiserate with my kid. The same principle applies to preparing for a sales call.

5. Feedback.  Lots of sales leaders think they are great at giving feedback; few, in my experience, actually are. The trick here is to make sure the feedback that you're giving your rep is focused on the job and not the person.  I've watched many, many sales leaders start with a phrase like:

• You know, you always do x.
• You should do Y.
• You should stop doing x.
• You’re the kind of salesperson who…
• X always happens on your deals.

Each of those is an attack on the person. Wouldn’t you consider it an attack if someone in authority said one of those things to you?

If any of those phrases sounds familiar, you might want to consider taking out the side comments that have to do with what the individual is or always does. You might also want to take out the word “should.” Truly effective sales leaders give feedback on the job, not the person. For instance:

• Would doing Y help?
• Have you thought about possibly doing Y instead of X?
• What would happen if you did Y next time?
• Have you tried Y?

When we fixate on what a salesperson is or what a salesperson always does, people get confused, and they feel rejected. That’s not good, because they take rejection personally. and then they don't improve their role performance.  We want to help our people maintain self-esteem and a positive self-concept.  It's a tough world out there.  They're already getting rejected 90% of the time.  We want to make sure we’ve pumped up their self-concept but at the same time giving them honest, helpful feedback on the job that they've done. 

This is my take on the five essential skills sales leaders want to build up to make sure that their teams are highly effective in the upcoming year.  Which one will you choose to make a personal priority in 2022?

Learn more about the key to sales leadership by reading this blog post.