Bag with money and red wooden heart on the scales.

People or Deals – Which Comes First?

What Type of Leader Are You?
This question can be posed in a myriad of ways; however, the main objective is to determine whether the aspiring sales manager is geared more toward managing the person or the deal. While most leaders would self-identify as people-focused leaders, experience tells us a different story.

Flies on the wall of team meetings, 1:1s and QBRs in the technology sales world are reporting in large numbers that it’s all about the deal. It’s often difficult to distinguish these meetings from traditional forecast meetings. Their stories are corroborated by their fellow flies who are eavesdropping on employee exit interviews, as well, where the popular mantra is “I’m leaving because I’m burned out. My manager doesn’t give a hoot about me. She only cares about the deal and her forecast.”

This dilemma is quite paradoxical since, according to DISC behavioral communication statistics, approximately 80% of participants assess to be more in tune with the emotions of people; thus, wired to achieve success through others. Is it the environmental conditions – i.e. the pressure of hitting the forecast – that compels sales managers to be more task-oriented and deal focused? A recent executive guest on the Coach2Scale podcast commented that the pressure is at the highest he’s ever seen. If you’ve closed out even a year’s worth of fiscal quarters, this is not a surprise to you.

Undoubtedly, as a manager you’ve spent countless hours in both individual and team meetings giving or requesting update after update on the same deals. Oftentimes, these meetings happen so frequently, there’s not even enough time to connect with the client so that the latest and greatest update can be refreshed. You’re exhausted and frustrated after providing multiple variations of your forecast to include your “best case,” “worst case,” “best-best,” “if the world ends,” “most likely” and, of course, your “gut.” Meanwhile, nobody can lucidly define what any of this means. All we know is that our boss, our boss’s boss, or one of the layers above them needs this info. Oh, let’s not forget the endless stream of email and Slack requests for the same info. While you’re at it, make sure it’s all reflected in CRM, too. Are we having fun yet?

Front-line Sales Managers Have One of the Most Difficult Jobs in the Company
This is not lip-service. Many did not know the realities of the role when they initially pursued it. In fact, this view was recently supported by a panel of senior leaders on the Rally Call, a podcast co-hosted by my friend and former colleague, John Feldman, that focuses on helping technology sales professionals have more enjoyable careers. Most sane people would rather poke their eyeballs out than be at the tip of this spear if they really knew what their responsibilities entailed. After all, these proud professionals want to inspire people, and solve problems. They don’t want to be labeled the dreaded “micromanager,” but they don’t want to be put in the “soft” or “pushover” categories either. Well, at least they can lean on their manager for help. Ha! Wishful thinking. The average CRO is in that role for approximately nineteen months. They don’t believe anybody really cares about their five-year plan even though they go through the motions to update that every few months. Exceeding quota and growing the business is the name of the game. Coaching the individual rep and developing their skills via a personalized and programmatic plan is a luxury. Hitting the numbers is the only way to survive. What would you do?

Human beings want to help other human beings. Extensive scientific research supports this theory. That this is sometimes difficult to believe is understandable; however, the reality of the situation for sales leaders is that your people drive those deals that need to be won. To be successful over the long-term, sales managers need to understand how to ignite the intrinsic motivation within each of their direct reports. This certainly takes some work; however, the rewards can be immensely rewarding on many levels. While there are many ways to approach this, here are three best practices to help achieve this balance.

  • Consistently hold 1:1s
  • Develop the person not the deal
  • Foster a culture of collaboration and sharing amongst the team

Best Practice #1: Honor Your Commitment to Holding Weekly 1:1s
These weekly 1:1s are the most important meetings of the week with each of your direct reports. They’re not fluffy “how did your fantasy football team do this weekend” meetings, but they’re also not “how many different ways can we discuss the forecast” meetings, either. This is your chance to show your people you care about them. Salespeople show up to work for their reasons, not yours. And, as you become better at uncovering the personal “why” for each person, you won’t have to guess at what motivates them. For the team to be consistently successful, everybody needs to show up for work each day as the best versions of themselves. When they don’t, everybody pays the price. Life can be hard at times. What’s going on in the personal lives of your people is going to affect how they execute at work. This regularly scheduled 1:1 time is the perfect opportunity to get out in front of problems and be better equipped to provide the proper support when issues inevitably arise.

To build momentum and trust, these meetings should be scheduled in permanent marker, not an easily erasable pencil. Avoid rescheduling because of customer calls, your stressful calendar, or a boss calling. This sends a message that you don’t really care. One of the best sales leaders I’ve worked with was reputed to never cancel his 1:1s. In fact, one of his direct reports commented: “I worked for him for three years and think he only rescheduled a one-on-one meeting twice during that time.” Your actions do not go unnoticed.

Lastly, the 1:1s need to be mutually beneficial. A litmus test for managers is to ask yourself (or ask your rep) what benefit they receive from these 1:1s. If you’re stumped for an answer, the 1:1s may require an overhaul.

Best Practice #2: Grow Your People, Not Just the Deal
Exceeding the number and growing the business is a top priority for sales leaders. This can only happen when deals close at an acceptable conversion rate. How much easier would your job be if you built a team of self-sufficient salespeople? Leaders help define the problem; however, they don’t need to solve them. Think bigger than just the moment and take time to understand what may be holding a deal back. Does a pattern emerge? For example, does your rep consistently struggle with getting access to key decision makers or discount too much at the last minute? Isolating the root cause of these problems, instead of trying to beat down the symptoms “whack-a-mole” style, can lead to powerful dialogue and self-awareness. Through effective questioning, you can help your reps self-diagnose the problem and offer their thoughts on potential solutions. From here, you can use tools like role-play to coach them to be more confident and better skilled to deal with these problems as they come up in the future.

This doesn’t require as much time as you fear. As you’re coaching your people through difficult scenarios, get them to practice aloud how they will respond to, say, a common objection. Allow time for specific, actionable feedback to be shared by both of you and then ask them to try again. Rinse and repeat as often as possible. You can move mountains in five minutes. Set expectations that this type of practice is supposed to be uncomfortable. The key is to keep it a light, nurturing, and safe environment.

In sales, we often practice “in the game” – in the meeting with the prospect or client. Think about how crazy this is. Would an accomplished musician, athlete or surgeon ever try something new for the first time when it mattered most? No way. They would have practiced so much that they don’t even feel the pressure. When you focus on developing your people, they will know exactly what to do and say at the right time – not just on the one deal but all the others that will follow. You’ve taught them how to fish!

Best Practice #3: Foster a Team Culture of Collaboration with Urgency
Take some pressure off your people. Nobody performs their best under stress. Oftentimes, their stress comes from believing they must have all the answers or do everything themselves. They believe it’s “sink or swim” and they’re on their own. This is where managing people and deals really comes together. Success doesn’t have to be a zero-sum game. Everybody on your team does something well. Look for opportunities to catch people doing things right and then promptly share these best practices with the entire team. Moreover, set the expectation that everybody needs to apply what they’ve learned asap.

For example, if you were to find an opportunity to bring the team together for a twenty-minute group coaching session around a specific topic on Thursday at 1pm, your reps could realistically be back on the phone with prospects and customers subsequently at 2pm, 3pm, 4pm, 5pm etc. And, they can try it again the next day – Friday – at 9am, 10am, etc. With clear direction and encouragement, they can each find numerous opportunities to apply what they’ve just learned before the weekend. Reps won’t master the new skill or technique in a couple of days; but they will begin earning and benefitting from the magical principle of compound interest that will pay meaningful dividends over time. Instead of each rep having their own “toolbox” to help them find their way, imagine if everybody contributed to the creation of a “team toolbox” that was consistently improved upon and available to all. Think of the benefits from this type of teamwork and culture. One leader I’ve recently interviewed was blown away at how willing each person on the team was to help their fellow team members. It truly became all about achieving team success by maximizing the effectiveness of each person on the team. Nobody feels left out. Celebrate, debrief, and share key takeaways for both closed-won and closed-lost deals as a team. There’s a ton to learn from both groups. Every opportunity is a learning opportunity.

In summary, people should always be priority one. Deals will follow. Hold sacred to your 1:1s. Develop the person, not the deal. And finally, foster a culture of collaboration and sharing amongst the team. Your pipeline will start accelerating immediately, with the compound effect of building on best practices and the team toolbox.