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Tom DiScipio

By Tom DiScipio

Jan 25, 2018


Executives and Leaders Inbound Sales
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Executives and Leaders  |   Inbound Sales

Managing a Sales Team: 7 Lessons from a First-Time Sales Leader

Tom DiScipio

By Tom DiScipio

Jan 25, 2018

Managing a Sales Team: 7 Lessons from a First-Time Sales Leader

I wasn’t always in Sales.

I graduated college with a degree in Graphic Design and Presentation and minored in Art. My first real job out of college was working as a production associate at a local sign shop, assisting with digital design and installation of signage.

Fortunately for me, the next step in my career was joining Bob in the early days of IMPACT, continuing the execution of creative work.

As we grew our client base, I got a taste of what it meant to be in direct connection with the client.

I truly enjoyed this part of the job and relished being able to help them dissect a complex challenge into a series of actionable steps, and then get them to take those steps with us.

It really didn’t feel like “selling” back then.

Fast forward a couple of years: IMPACT has grown dramatically with the addition of a full-time sales rep, dedicated to prospecting and onboarding net-new clients.

Over the years, we had a number of people go in and out of that sales position with generally good success. However, in late 2014, after the latest sales hire moved on, Bob approached me and said, “We need someone to do sales. Can you do it?”

As the Creative Director at the time, and fairly unaware of what an official “salesperson” should know and do, I was a bit apprehensive in my reply. At the same time, I saw the need for the organization and was excited about being the person to establish the direct relationships with our potential clients.

“Yeah, you got it, Bob.”

Fast forward again a couple of years and I managed to hold my own and even excel in the position.

IMPACT’s topline sales and monthly revenues had grown at a rapid rate. With larger, more aggressive objectives looming in our future, we decided it was time to expand sales beyond just me; to grow the sales team and for me, personally, to grow into a sales leader.

Hence, the title of this post…”a first-time sales leader...”

7 Lessons on Managing a Sales Team

I chose to focus on lessons that go beyond the typical metric and quota tracking stuff that fill a normal day in the 
#saleslife. Most sales managers already know there are numbers to hit and managing to those help everyone know where they are and what they have to do to be successful.

The lessons I share below come from the many mentors and leaders I’ve had the chance to learn from -- but adapted for a sales environment.

As a first-time sales leader, I know there are many more lessons to learn and more so now than ever, I’m leaning on my team to learn from them.

So for those who are going through this journey or have already seen the end of the movie, please add to the conversation by sharing the most valuable lessons you’ve learned as a sales leader in the comments below.

Let’s dive in.

1. Help them stay organized… beyond the CRM

Sales folks tend to spend most of their time in their Customer Relationship Management platform (or CRM) - the area where they can keep track of all notes and details regarding the deals they’re working.

While this promotes staying organized at the deal level (tactical), it does not necessarily help from a high level (strategic).

Operating in a new business role is incredibly time-consuming and where that time can be allocated is extremely variable.

Should a prospect not show up for an hour-long meeting or another come out of the woodwork with a “Yes! We’re ready to sign the agreement,” can have a dramatic effect on how a sales rep manages their day (and night).

To help our sales team stay organized outside the minutiae of the deal, we’ve instituted an agile project management framework called Scrum which helps create alignment throughout the team. With Scrum, reps have to plan in weekly increments in a shared “sprint.”

This makes them accountable to the rest of the team for completing planned activities, but also remain adaptable to change.

Planned activities might include, “Conducting an Exploratory Call with X company,” or “Building a Statement of Work for Y company.”

Tracking these activities within a global project management tool (like Jira) creates high-level visibility for both reps and myself into when a deal has the potential to close or when the written agreement might get sent.

2. Let the rockstars be rockstars

I’ve been incredibly fortunate to have a sales team filled with absolute rockstars with potential and abilities far beyond my own.

As a manager who began as a “doer,” I initially tried to shape each rep’s approach and demeanor based on my own personal process and success. However, I soon came to understand that the varying personalities and processes of my team members should be uniquely preserved, and in many cases, just left alone.

The job of the sales leader or any leader, in general, is to enable their team; to create the operational guidelines (not rules) and decision-making space to allow their team to be rockstars in their own right. It is NOT to micromanage them to a personal definition of “how to do X.”

3. Never miss a One-on-One

The benefits of having one-on-ones, or individual meetings between you and those you manage, are widely-known.

In many of the managerial books and podcasts that I’ve listened to, they are considered the most important piece in management and for good reason. They foster the manager/employee relationship and give managers the ability to keep a pulse on how the the rest of the team is feeling.

In the context of this article, I wanted to focus on one benefit in particular -- they are the ideal time for leaders to get the first-hand and constructive feedback necessary to become aware of personal shortfalls and areas for improvement.

Being the best leader for another means you must first become the best version of yourself.

While you’re giving your reps candid feedback, allow them the opportunity to do the same. You won’t regret it.

4. Go out of your way to provide feedback on calls

This might not be anything new for many of you, but I hope you’ll focus on the “go out of your way” part of this lesson.

While one-on-ones might be the best way for salespeople to provide feedback to their managers, I believe the best feedback and growth opportunities lie in the manager actively listening or participating in rep’s calls with prospects. (Something our sales consultant, Jack Carroll has done with us since day one.)

Despite having an incredibly full calendar most weeks, I will (in most cases) join calls that a rep asks me to be on --or I will snoop around on my reps’ calendars for calls to join… Muahaha.


I recently joined a sales call as an active participant with one of my reps.

Sitting across from him at the table, I had my computer open with a blinking cursor on a blank page in Evernote. During the call, I took notes on important things the prospect said, but I also listened intently to what my rep is saying and how he conducted the call as a whole.

Taking into consideration the philosophy of “letting rockstars be rockstars,” my goal is not to say, “I would’ve done it this way;” Rather, it’s to share fundamental sales tactics in the context of the conversation.

“In case you didn’t know, I was taking notes on the call about your performance.”

Usually, I’ll get a little smile and an, “okkkk…”

“Are you okay if I share some of the feedback with you?”

Truly passionate sales reps with a continuous learning mindset get excited about this part and will say, “ABSOLUTELY.”

Jumping back to my experience, the outcome of that call and feedback session hosted just after was absolutely incredible. The next call that rep had was a home run with about 90% of the tactics from the feedback session put into play.

Tip: Should your calendar not allow you to join an hour-long call plus a 15-minute feedback session, ask your reps to record all of their calls and keep them in a database for future review on your own time. Then use the feedback notes from that review in your one-on-ones.

5. Have them read The Challenger Sale

I first discovered The Challenger Sale from some folks at HubSpot. They mentioned that they’re all required to read this book and after reading it twice myself, I can see why.

This book not only changed my understanding of the makeup of a successful salesperson, but it created a much deeper sense of what prospects long for in the person they’re interacting with.

Without diving too deep into the book, The Challenger Sale model is built upon three principles that successful “Challenger” salespeople embrace:

  1. Teach: The rep must be able to provide insights or ideas that challenge prospects to re-think their business, goals, or aspirations.
  2. Tailor: The rep must tailor their message to resonate with both the prospect’s personal motivations as well as the business objectives.
  3. Take control: In a non-bullying way, the rep must be the sherpa of the conversation, always leading back to the discussion of value, standing firm on typical objections such as price.

Aligning with these three principles are critical for a reps ability to lead a compelling and a differentiating sales conversation. The Challenger Sale has given our team the framework and the language to become the prospect’s trusted advisor and has given me the foundation for coaching my team.

6. Be available when they are

As mentioned previously, a salesperson’s time is not only limited because of meetings it varies greatly based on the availability and commitment of prospects. What might be a lighter day could turn into the busiest day of the week within an hour. Trust me, I’ve been there many times.

Fleeting moments of availability means that reps’ days can very easily transition into the night which is when you see recap emails going out, follow-up emails being sent, and contracts being built/sent. It’s an inevitability in a sales position.

This lesson is not to promote the idea of consistently working 10-12 hour days. Rather, it’s to foster camaraderie with your reps.

They’re not the only one in the trenches. Let them know you have their back when it’s time to get work done. Be available during and after hours to re-prioritize or offload tasks, or even get hands-on and help complete their work.

7. “Clear the way” for your team

Now, this lesson is an extension of lesson six, and may or may not be a good fit for all in a sales leadership position.

Leadership is not a universal methodology - it comes in all styles and interpretations. For me personally, my natural tendency is to operate within a Servant Leadership capacity, a philosophy and term coined by Robert Greenleaf in 1970.

Greenleaf describes Servant Leadership in many ways, but the part that resonates most with me is, “[In comparison to “traditional” leadership] The difference manifests itself in the care taken by the servant-first to make sure that other people’s highest priority needs are being served.”

My visual interpretation of this is like walking through a dense jungle, just ahead of the pack (my team) with a machete, clearing the trees and brush so they can see the path and advance forward.

While I don’t believe leadership just ends with the Servant mindset, I’ve come to believe this style of leadership is valuable for my sales reps because it allows for the removal of any impediments that might otherwise slow them down from what they really want to be focused on: advancing a deal and hitting their numbers.

As a manager, this translates to getting truly hands-on with things like drafting complex proposals, acting as a lawyer to help with redlining contracts or even setting up calls on the rep’s behalf, among many other tasks.

It means doing what it takes to set your team setup to do what they do best.

To wrap up…

Leadership is an endless learning process. As our Chief Operating Officer, Chris Duprey would say regarding growth as a leader, “Be a student of leadership.”

My personal growth as a first-time sales leader managing an amazing team has lead me to share some of the lessons I’ve learned at the starting of my journey:

  • Help them stay organized beyond the CRM: Help your sales folks align their own higher-level, longer-term priorities with the rest of the teams’ by implementing a project management framework (like Scrum) that holds them accountable, allows them to execute the work in digestible chunks, and allows their workload to be flexible based on a rapidly changing schedule.
  • Let the rockstars be rockstars: Many managers have come from a role of being a “doer” with a legacy of success. Remember that the “how” to a successful endpoint can vary dramatically based on an individual reps personality, style, and characteristics. Foster that style, create the conditions for success, step back, and the rockstars rock.
  • Never miss a one-on-one: Being the best leader for someone else means being the best version of yourself. The majority of your improvement will arrive through constant and critical feedback from one-on-ones with your team.
  • Go out of your way to provide feedback on calls: Your participation or active listening during prospect calls followed by a feedback session is the most effective and real-time way to illuminate where your salespeople can improve.
  • Have them read The Challenger Sale: This book describes the data-driven formula for the abilities of a successful sales rep and a solution for how to become one. It’s immediate ammunition for a rep’s mastery of sales.
  • Be available when they are: With the extreme variability of a salesperson’s time, they may only have time to get actual work done or connect with you at odd hours of the day or night. Be relentless about making yourself available for them.
  • Clear the way for your team: Your team is desperate to stay focused on bringing new clients into the organization. Remove any impediments that might slow them down, even if it means doing some of the work yourself.
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The one and only They Ask, You Answer conference. Reduced rates on sale for a limited time.