Great Sales Skills Are Great Leadership Skills

I spy spiderwebs, skeletons, and squashes popping up around my neighborhood. But what’s the other “S” word that’s just as scary to some? Sales. 🙀

Many of us cognitively understand that we are selling every time we try to get a new hire approved, a new software purchased, or a direct report to do what they said they were going to do. Here’s a more tactical look at how six great sales skills translate into great leadership skills that show up in my coaching, and likely, your work, all the time.

If you’ve been picking up what I’ve been putting down, please help the Inner Radio Newsletter grow by sharing it with your communities!

1. Great Sales Skills Are Great Leadership Skills

So you’re a sales coach?

In a way.

My background is in sales, and there are times I help teams with their sales storytelling and process, but I do not exclusively support leaders and teams formally in sales.

The majority of people I work with are not in sales formally, but are in roles where selling is crucial to their success. The result is that sales concepts come up in our coaching sessions over and over again. I’m on a mission to destigmatize sales and spread the word that embracing sales makes us more effective leaders. Here’s how:

Expect Roadblocks

In sales: There’s no perfect sales process. When things are going too smoothly I start to get suspicious that I’m missing something and there’s a surprise I haven’t identified yet. Every sales process follows a similar structure (Discovery, Demo, Proposal, etc), but inevitably some wrench gets thrown into the mix. Your champion at the company leaves. Budgets get cut. A new decision-maker appears out of this air. Political tensions and egos show up. This happens so often that it no longer becomes a surprise wrench, but an anticipated one. What that means for the strong sales person is they don’t become flustered when faced with roadblocks. They move quickly to acceptance and finding a path forward.

In leadership: Surprise! Surprises happen. The unlearned leader is in disbelief. “I can’t believe they would say that in the meeting! I can’t believe they would change their mind!” Actually you can. Because it happens all the time. Assume a wrench will appear at some point in whatever project you’re managing. Resources, motivation, and knowledge may change. Don’t waste energy in disbelief when they do.

Call It Quits

In sales: Strong sales people don’t waste time. They disqualify leads ruthlessly so they don’t waste their time or anyone else’s. Strong sales people disqualify when they’re not a great fit – the prospect is trying to solve a different problem than the product solves for. The prospect isn’t serious about making a decision right now. The right people with the right influence aren’t driving the effort. This is an exercise in discernment.

It also means: Being willing to walk away from the deal. A strong sales person always has to be willing to walk away or there’s no negotiating power. They have to fight the temptations of sunk cost (oh put all this energy in, I have to make it work no matter what!) As mentioned, things change, and if it’s no longer a good fit, be willing to walk away.

In leadership: How much time do you waste doing things that other people should be doing? Do you go to meetings with no agenda? What are the metrics for you to say yes to something? Be ruthlessly discerning. Your choices are contagious. If you take on things you shouldn’t. Others will follow.

Be willing to walk away. I see this most often when leaders wait way too long when someone is underperforming to have the conversation, to convey the urgency, to say – this might not be the right role for you anymore.

Fall on your face

In sales: It’s not a matter of IF you’re going to have a terrible demo or step in it at some point in a sales process, it’s a matter of WHEN.

• You’ll be so close to closing a deal and then bring up a random point that confuses the buyer and overcomplicates the process, delaying your deal possibly forever.

• You don’t dig enough into the stakeholders and the head of IT comes in at the last minute and derails the purchase because they’ve been running a separate buying process in parallel.

• You PISS OFF the senior decision maker in the room with something you said.

You may have just fallen on your face, but you also have another call scheduled 15 minutes after the disaster. Strong sales people regroup quickly, incorporate the feedback (it’s valuable data!), and move on.

In leadership: A fear of making mistakes will stymie your career. You will miscommunicate. You will choose the wrong approach. Remember, it’s not IF, but WHEN. Living in fear of making mistakes is a mistake that often results in paralysis and a meandering, confused team. So WHEN it happens, regroup, incorporate the feedback (it’s valuable data!), and move on.

Words Matter

In sales: The phrasing we use to introduce ourselves, the insights we share, the use cases we highlight, the questions we pose, the ask we make at the end of the call all matter. Strong sales people practice.

In leadership: Talking about how you’re going to say something is different from actually saying it. Practice actually saying the words and see how they feel coming out. Whether it’s feedback you’re delivering, a meeting you’re facilitating, a presentation you’re giving, practice the actual words, please.

Challenge Assumptions

In sales: Your Buyer may come in with assumptions of what they need, and your job is to help them see things more strategically to actually solve their problem. That might mean helping them consider additional metrics to vet solutions, or think through how to navigate their internal organization for approval.

In leadership: Your role is to develop other people’s thinking, not tell them what to do. Remember, “do as I do” breeds dependence, not competence.

Dig Deeper

In sales: When a strong person shares pricing, the Buyer may experience sticker shock. With sticker shock comes a host of excuses that have nothing to do with pricing (example: suddenly the project is no longer a priority). A strong sales person knows how to dig deeper and uncover the root of the issue (example: actually, the Buyer doesn’t know how to ask their supervisor for that kind of budget).

In leadership: When your direct report has an issue, listen for their pain. Dig deeper to understand the root of what’s compelling them to come to you. At first they might not tell you (or even be aware of!) the real issue at hand.

Sales skills are learnable skills, which means leadership skills are learnable skills. This certainly doesn’t mean you’ll get it right every time (remember: fall on your face), but there is a path toward mastering the craft.

2. Recommendation

Setting the Table by Danny Meyer

The restaurant I managed back in the day was not a Union Square Hospitality Group restaurant (Danny Meyer’s restaurant group). However, I greatly admired his team, and Union Square Cafe is still one of my favorite places in the city to enjoy a meal for one at the bar.

USHG adopts an “enlightened hospitality” philosophy where staff are trained to prioritize their relationships with one another and then extend that hospitality to everyone else to the business. I don’t think it’s a huge leap to see the application of this approach to other organizations. Dysfunctional team dynamics bleed into every other relationship our businesses touch — our customers, our partners, our investors, you name it.

He breaks down “technical job performance” and “emotional job performance” – which I would hugely appreciate to see more often in performance reviews and given the appropriate weight.

3. The Goings On

On the topic of restaurants, I had the chance to visit Blue Hill at Stone Barns in Tarrytown. We toured the farm’s gorgeous grounds, learning about their crop rotation cycle, high hydration bread making, and partner farms. The delight of the evening was the surprise mid-meal field trip into the heart of the kitchen to see masters at work. There was intention, focus and precision behind each movement book-ended with a reverberating, unified “Thank you, Chef!” as we entered and left the room. I was reminded that most of the time we see the finished polished product that arrives beautifully at the table (or at work). We don’t often get to see behind the scenes, even though that’s where so much magic happens. It was as if the restaurant shared a little secret with me and I felt that much more connected to the experience from that peek.

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