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A strong, high-performance sales team is critical to a successful business. But what makes a sales team truly great, and what strategies can leaders use to create a team that's highly successful? To address these questions, we're talking to CROs and sales executives about "How To Turn a Good Sales Team into a Great One." As a part of this series, I had the pleasure of interviewing Nancy Medoff

Nancy Medoff

Nancy Medoff

After close to three decades of walking the talk in corporate sales leadership, Nancy Medoff, best-selling author, keynote speaker, top 25% podcaster and sales coach has literally “written the book” on workplace confidence. Confidence impacts outcomes and ‘Unmute Yourself and Speak Up to Stand Out’ is a step-by-step communication playbook for sales professionals who are ready to level up and own any room. Tactical tools, a Power Positioning Template, and real life, relatable anecdotes provide the tools we all need to speak up to stand out and communicate with clarity and confidence when the stakes are high.

Thank you for doing this with us! To start, can you tell us the 'backstory' about what brought you to this career path?

I actually fell into my thirty-year sales career!  When I graduated from college, I thought I was applying for a catering sales role in a big hotel in Boston. I should have read the job posting better because the position was actually working the back of the house, where I stayed for a few years. I used to see all the glamorous sales people, walking their clients around the hotel and I thought “I can do that!” So I started in entry level sales and worked my way up to VP of Global Sales.

I loved the business of sales and understanding that there is a process, it’s not only about relationships. Sure, relationships are important, but there is big business behind selling. The highest performers move the relationship beyond dinners and entertaining and become trusted advisors in many areas of their client’s business.    

Can you share an interesting or amusing story that has occurred to you in your career so far? What was the lesson or takeaway? 

Such a great question! Lots and lots of fun stories (because let’s be honest, selling is FUN) and I’m going to share a story that’s about significant lessons. It’s a little emotional for me, because it was one of those “sliding doors” moments where you actually see your life path change:

I was leading a global sales team in the U.S. for Marriott, and my SVP asked me if I would consider moving to Asia and living in Hong Kong, to lead the global sales team for Hong Kong, China and Japan. I had been to Asia a few times and always wanted to live there. I was single, had nothing tying me to the U.S. and to say I was honored to be asked is an understatement. I also ended up turning the job down. Here’s why:

I knew very little about the culture, and while naturally I would learn, I was a new leader and did not yet have the emotional maturity to lead a team (or myself) through this kind of change. I knew that in my heart.  

I had no network. In the States I could call on a number of colleagues and mentors who could help me to work through whatever issue I was facing. In Hong Kong, I had yet to develop these relationships and while I knew they would come, I wasn’t sure they would come quickly enough.

The team there needed someone they could relate to and someone they could bond with. I was confident that I brought a lot to the table and would have been successful however I felt they needed a local. Someone who knew them, knew their clients, knew their business and knew how to quickly diagnose and help them to fix problems.  

Last, this would have been very, very lonely. Yes, it sounds glamorous and exciting—and it was. It was also a 23-hour plane ride, a completely upside time zone, a very difficult language and not one but three new cultures and nuances.  Remember—I had no support network there yet. 

The lesson? Always trust your instincts and don’t be afraid to speak up, even if you think it’s an unpopular opinion (it wasn’t by the way—in this case my boss appreciated the feedback and perspective and hired a local sales leader who brought the team together and did an excellent job).  

Are you working on any exciting new projects now? Tell us about it!

I’ve combined the success of my team-based selling program with my confidence skills training to create a new training and coaching program specifically for women in sales.  We all know that confidence impacts outcomes. But did you know that under-confident negotiators only have a 20% success rate? That’s correct—20%.

This unique program leverages the natural connection between my passion for empowering women and the impact confidence has on negotiations. Women have made progress in recent years, but make no mistake—the confidence crisis is still holding women back and this is impacting sales. You may not like it and this may be hard to hear, but these are cold hard truths. 

My program debunks the confidence crisis & positions your sales team to dominate as we leverage women’s inherent strengths to make them better negotiators, close on more business and stop leaving money on the table.  

None of us can achieve success without some help along the way. Is there a particular person you're grateful for?

Oh, so many, and the one I will share today again goes back to the story I shared earlier. I remember being afraid to tell my big boss that I didn’t want to accept the position he was offering me. I was certain that he would be mad, disappointed and that he would never ever offer me a promotion again. At the time, I was very young and had not yet stepped into my strengths and convictions.

My boss at the time, Gail Wargo helped me to realize that just because someone has more experience than you, this doesn’t mean they always know what’s best. And that catastrophizing the outcome will always create undue stress on yourself. I never forgot that advice and of course I will always be grateful.

Can you tell us a bit about your experience leading sales teams? How many years of experience do you have, and what size teams?

I’ve built, led and trained global sales teams from 12 people to 200. I’ve also led and built inside sales teams up to 120 people. The largest sales goal we ever surpassed was in the several hundred million range. 

What do you think makes a sales team great? What strengths or characteristics do you try to cultivate?

The difference between a good sales team and a great sales team is that extra 10%.  What’s the fire like inside of the team? Is there a spark? Are they passionate about what they do and who they serve? I always hire for attitude and behavior because I can train anyone how to sell, what can’t be taught is passion. 

As with any department, there can be a lot of different strengths, weaknesses, and personalities. How do you manage such diversity on an individual basis? Is there such a thing as a blanket motivator?

Diversity of strengths is what makes the team great! Your team needs different skill sets so that together, the sum is greater than the parts.  

I always try to tap into each individual’s motivator and also understand that high achievers are not always motivated by money. At a certain point, money is not the biggest driver behind their motivation. Discovering what makes them tick and tapping into that inherent fire is what motivates the individual. 

As for the team… there is absolutely a blanket motivator. Winning.  

What strategies have you tried to increase motivation, engagement, and productivity? We want to hear it all, the stranger, the better!

I have dressed up like a lobster during a team clam bake, I’ve jumped over desks in full costume as a sales ninja, I’ve been Mrs. Claus and I’ve turned more cartwheels than I can count. 

I’ve also rolled up my sleeves and made hundreds of calls to high value clients, I’ve flown across the country for a cup of coffee and a closing, and I’ve spent several hundred hours helping the team to increase their confidence—in themselves, their relationships, their ability to reach the desired outcome. Confidence is a skill and like any other skill, with training and practice anyone can master feeling confident. Anyone. 

Of all the strategies you've tried, which did you find to be most effective? Did this have a direct correlation to sales? 

There is one strategy that without a doubt is the most powerful skill you can master to close more sales. It is also the simplest. Two little words that will change a whole lot:

"So. What."

You can have the greatest product or service in the world. You can show the value time and time again and at the end of the day I ask… “so what”? What specific outcome, result or process improvement can the client expect as a result of this value proposition? The more specific the better. Revenue increase? Client satisfaction? Process improvement? SO. WHAT.  What’s the bottom line to their business? 

Can you tell us about a time that your sales team outperformed their targets? How high over did they go, and what was that like for everyone? 

My teams have always outperformed so there isn’t really one specific example. I share this with confidence, not arrogance and I can tell you with certainty that discipline will always trump motivation. Sure, it’s not as sexy to talk about discipline, and detail (us sales people are not always hot on details), and managing the every day but truly the basics will always come through in tough times. 

Great things often take time. What do you think is a realistic timeline to take a sales team from good to great? 

Salespeople are often impatient (and by salespeople, I mean me) and this really will depend on the team and the situation. A newly forming team? I was able to lead one team to $4.3 million in prospects in six weeks. A seasoned team? This will likely take a little longer and will depend on the situation and how much time, energy and money is invested in building the team’s skills and honing in on their strengths. 

Based on your experience and success, what are the five strategies that will help turn a good sales team into a great one?

1 . Team first. I led a global sales team for close to two decades and while we all had our own individual motivators, we always cared deeply about the success of the team as whole. Weekly team calls, recognizing wins regardless of how big or small, and sharing our stories about both the good and the not-so-good brought us together.

2 . Back to basics will always drive results. Often times we get caught up in the hunt, and perhaps try to skip a step or two in the sales process, and this is when those gaps will cost you and the team.  There are many versions of the five or seven step sales process out there so use what’s best for you and toss the rest. Then live, eat, and breathe the process with your team. 

3 . Recognition is critically important. How often are you recognizing the team? The individual? Are you sharing wins with your senior leadership? Are you taking the time to personally thank and recognize each team member for their contribution? It’s easy to get caught up int the next big client win, so make sure you’re celebrating the small ones too. 

4 . You must invest in leveling up the team’s skills and their confidence to take the team from good to great. What got a great salesperson to where they are will not get them to where they need to go. A team of thoroughbreds needs new tools, new ways of thinking and new ideas in order to thrive.

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5 . Clear goals and expectations. Nothing will demotivate a high performing team faster than messing around with their goals. If you want the team to perform, they need clear revenue goals early in the fiscal year. Include stretch goals with commensurate rewards. 

Lastly, if you could inspire a movement that would bring a great amount of good, what would it be? You never know what your idea can trigger!

Confidence impacts sales. You MUST arm your team with true confidence and true belief that they will succeed. I’m not talking about bravado and rallying. I’m talking about the knowing deep inside and that spark that says “I know I’ve got this”. 

How can our readers further follow your work online? 

My website, on LinkedIn and if you’re looking for a weekly shot of confidence you can follow my podcast or join my confidence collaborative here!

Phil Gray
By Phil Gray

Philip Gray is the COO of Black and White Zebra and Founding Editor of The RevOps Team. A business renaissance man with his hands in many departmental pies, he is an advocate of centralized data management, holistic planning, and process automation. It's this love for data and all things revenue operations landed him the role as resident big brain for The RevOps Team.

With 10+ years of experience in leadership and operations in industries that include biotechnology, healthcare, logistics, and SaaS, he applies a considerable broad scope of experience in business that lets him see the big picture. An unapologetic buzzword apologist, you can often find him double clicking, drilling down, and unpacking all the things.