Maestro Spotlight on Lyndsay Dowd: Selling and Leading with Intention

COACHING AND LEADERSHIP

Lyndsay has worked nearly her entire career in sales, and 23 years of that was spent climbing the ranks at IBM. Beginning in customer service, she ended up at the executive level, working with multimillion-dollar contracts and leading one of the most successful teams in the company.

When I asked what her secret sauce was, she spoke about heart. Lead with heart, she says. When you berate people and create this immense pressure, what you really do is incubate a culture of anxiety. When you lift people up and support them to do the job you hired them for, they can do wonderful things.

And that is the basis of the resilience-based podcast that she runs, Heartbeat for Hire. The slogan? Heartbeats not headcount. It’s about seeing your workers as people, she says, and is the foundation for her two main principles in coaching and creating culture. The first: offer the most fun work environment. In a world where everyone loves to change jobs and gets bored after a few years, having a place people love to work is essential, and why would you not want this for yourself and your workers?

Second, DO NOT MICROMANAGE. Micromanaging is the fastest way to kill your team’s soul. To micromanage is to say to your team, I do not trust you—I do not trust you to manage the process or do what I am asking. It also makes no logical sense. If you hire someone you believe can do a job, let them do the job. If you had the time and energy to give a job your focus, then you would do it yourself. And if you don’t trust who you hire, then you need to fix your hiring process.

A coach’s job is to frame problems differently to get unique solutions from the workers who have the skills and time to come up with unique solutions. Lyndsay shared an example of her own.

She was working on a deal, and the relationship with the client was poor: low engagement, the CEO was uninterested in meeting with the team, etc. Lyndsay went to her manager and said she had a new way to try and interact, a new way to work with them. The manager’s response? “I’ve got your back. Now FLY!”

This gave Lyndsay and her team wind in their sails to take a new approach. Through their creativity and new-found collaboration, they closed a 23-million-dollar deal and completely changed the relationship with the client. The CEO now regularly engaged, the relationship changed, and that is what made the deal possible.

Trusting your workers gives them psychological safety. Work becomes a space where they are comfortable enough to think, grow, and innovate. Psychology tells us that when people are in stressful environments, their brains go into survival mode. It’s something you can see with children in school and adults at work. It’s not an environment that promotes growth and new and better ideas.

You hire people to be good at what they do, so let them be good at what they do. Have intention with your hires, then have intention with letting them work in the way that is best for them.

(NOT) GOING FOR THE KILL

Intention is not only relevant for leading and coaching. It’s also relevant for sales professionals focused on the sale. Week in and week out we discuss ways to close more sales, and this week Lyndsay shines light on how our mindset and intention make a difference.

Don’t go for the kill, she says. It’s the biggest mistake she sees, and the easiest way to kill or stall a deal. What she means by that is to not simply go into a call and immediately try to close the deal without any rapport or lead-up (yes you should always be trying to close a deal, but a thing rushed is a thing done poorly). I love stories, and Lyndsay gave me a great one, one that explains exactly what she means by not going for the kill.

Lyndsay had a friend who was trying to engage with a large company—a company where no one had been able to reach the executive director despite ample effort. Instead of continuing with the same approach, with support and trust from her manager, the friend tried something different.

She found out the director would be speaking at a conference, had the company pay for a ticket, and went. She sat, she listened, she waited all the way until the Q&A was finished, until she was one of the last people in the room, and then approached the director.

“Hi, I’m Sam,” the friend said. The director was flushed.

“Oh! I know you’ve been trying to reach me, it’s just…” but the director wasn’t able to finish.

Sam cut off the director and said, “No, no, it’s not that. It’s just, you’re also blonde, and I’m new to the area and have no idea where to get my hair done.”

The director was a bit surprised but clearly more at ease from the personal question rather than feeling pressured by something related to work. The director said where she got it done, and then Sam let the seeds she planted grow.

“I’d like to treat you to your next appointment, and I’ll book us together. Would you be willing to do that? And we can spend some time together?”

Sam booked the appointments, got THREE undivided hours of the director’s attention, and closed the deal. A six-figure deal that, all said and done, cost only $700 in leads.

It’s a story so beautifully set in having a culture to promote unique approaches, but also Sam having the patience to not go for the kill. It’s about listening to the prospect, getting to know them so you can know how they operate, their needs, and then being able to efficiently propose solutions that make sense to them. You slow down to speed up and will actually close deals faster.

The real lesson? Go blonde.

BEING YOUR OWN BRAND

The last topic we discussed tied to intention was the self. Lyndsay mentions how easy it is to forget about our own personal branding. People always think about the brand or product they work for, that elevator pitch, but often they forget they also are a brand, a thing worth pitching for, and that the benefit to that pitch is two-fold.

The first is that when you can advocate and articulate why you are a good sales professional, you will instill confidence in buyers. The first thing 90% of people do when you first reach out, if they are interested, is look up your LinkedIn profile. If your personal brand is solid, prospects are more comfortable and you’re more likely to close a deal. If your presence and brand are nonexistent, this creates doubt and fear in the deal.

Second, says Lyndsay, is that there is no such thing as job security, there is only career security. You have to build it for yourself. You have to use your own voice and build your expertise. LinkedIn is a great place to do that. Lyndsay actually teaches a great workshop on how to better leverage LinkedIn. When you build confidence around yourself, you build confidence in deals and in job offers. It’s about being intentional.

Our conversation ended with Lyndsay saying that to grow your brand and work ethic, you need to be willing to listen and grow. That applies to every level of sales, from the sales professional seeking work, all the way to the CEO looking for hires.

If you want to succeed, you need to be intentional and willing to listen and learn. You need to let people work and let people lead. Think creatively, and recognize that growth is the key to success, and it does not come with the same old ideas day in and day out.

Special thanks to Lyndsay Dowd for letting me pick her brain last week and supplying the anecdotes and wise tidbits for this week’s bundle of learning! You can meet other members of Maestro on our team page.