I played golf with a few of my buddies over the weekend, all of whom are career sales guys. At one point one of them made an interesting statement. He said, “Sales would be the best job in the world were it not for Sales Managers”. He then went into a long tirade of exactly what he meant by that, most of which I tuned out because I was lining up a 7-footer for birdie that would pay out substantially in our Wolf Hammer game.
But it did get me to thinking afterward: It’s easy enough to talk about the ‘Horrible Bosses’ we’ve had, and all the things they did that made it so. But what about the flipside? What are the best Sales Managers doing differently?
The best leader I have worked for to date was able to “differentiate” between each rep on what made them tick, what motivated them, and then coached them differently instead of a since approach. Everyone has different motivating factors to sell, so I feel it’s vital to understand your reps inside and out, and then work with them differently based on their needs, their goals, their aspirations, and their motivations.
The thing I’ll always remember about my best sales leader is that they workshopped the lost deals our team had even more than those we won. It was all about learning from failure, not feeling defeated by it.
We did these sessions where we walked through the milestones of the process and I always got a lot of value out of the different perspectives shared. Others saw things that I didn’t pick up on at first, and vice versa.
I think a great sales leader should always bring people together to move forward as a team, rather than look back and just point fingers.
the best sales leaders that i’ve had, I knew they had my back. They were the first to roll up their sleeves and jump in the trenches with me. Being in the trench with me meant that if it ended up being a loss, the post-mortem felt collaborative not accusatory with actionable lessons to try next time.
Their willingness to go out of their way to support me, my efforts and my customer’s outcomes meant I went out of my way to help them if I could. Respect is a two-way street.
I can think of a Sales Leader, that I had at Oracle, that differentiated herself consistently: My hiring manager, Jaclyn Kurtela, who ALWAYS thought outside of the box and anticipated the objections, prepped for the responses, and was tenacious in her questioning. She taught me the art of “Being prepared”, organized, and to expect resistance, and to overcome objections. Great sales people are always prepared and always thinking two steps ahead of their prospects, during the sales cycle.
One of the best leaders I worked with was someone who empowered me to think and act independently, but was always there to provide valuable guidance and advice as needed. This was particularly useful when trying to develop pricing scenarios to present to clients. I would spend hours coming up with models that resonated with me and accounted for many different scenarios and permutations of what a customer might need. I’d then show it to him, and because he was so experienced with this stuff he’d be able to very quickly analyze what I had crafted and come up with suggestions and alternatives that were immediately better than what I had, and would make the proposals more sellable and valuable for our company. It was all based on his experience knowledge of our solutions, the nuances of how to position something, and his expertise with financial models. The point here is that he was someone from who I received value, and as such I would enthusiastically bring problems to since I felt I’d get something useful out of our interactions. This is in stark contrast to many other previous managers, who obviously were just pushing paper and reporting upwards without offering much in return.
One of the sales leaders that I worked for had a ton of experience in the industry and would always make it a point to share best practices that worked for him. He continued to call on customers in his leadership position. He would give me ways to practice and up level weak areas and nudge me to try difficult or new approaches.
Great leaders, Sales and others, are genuine relationship builders and help their team explore and solve problems through active listening and coaching, rather than preaching “how to’s” from a soapbox.
I’ve juggled so many jobs in the past, and the common denominator between every good manager I’ve ever had is that I always knew they had my back. I always knew my best sales manager was in my corner, whether he was pushing me way outside my comfort zone or was encouraging me to be better. It has always been “this is where you are, this is where we agreed you should be, let’s work together on this.” Great guy.
The best sales leader I had would let me be “me”. He valued the differences between the team members as we were all mature and experienced folks, and used different techniques to get the best out of us.
The best sales leader I have ever worked for has been my mentor for over 33 years. He was the one who convinced me to stop being a sales engineer and to become a salesman. He took me out on calls to model behavior and then turned the calls over to me to continue discovery and conversation. He taught me to always be confident about my value to customers. He gave me room to fail and learn, never chastised me, always coached me and raised me up. I worked with him at five different companies and would drop everything and follow him again if the opportunity arose. I always learn from him, and that’s made me a better salesman and better coach and leader. Now he’s more like an older brother.
The best Sales leader I worked with (did not report to them directly) were unique in the energy and pace they brought to every conversation. Their presence in the sales pursuits made everyone move faster, get to answers faster, and be better prepared that the team would be without them.
At the strategic level, they were the best prepared team member on all counts. Their research of the customer’s business, executive relationship nurturing, and making customer executives feel they are becoming personally successful by partnering with this sales leader.