This is the first installment in a three-part series on being bold.
January 05, 2022
By Rachel Smith
We’re starting the new year focused on being bold, which honestly has me a little bit nervous. Why? Because there’s a lot of stuff out there on the internet about being a bolder person that’s, well, I’ll be bold right now and tell you—it’s trash.
First of all, there are way too many images of people jumping out of planes and scaling cliffs. You should not be deciding you want to rappel into a canyon because of something you read on a business blog. Second, there are a lot of vague suggestions of what you should do to embrace boldness, like, “do something unexpected.” Okay, unexpected like breakfast for dinner, or unexpected like sell the house and move to Paris? I need a little more to go on.
Many of the suggestions for becoming bolder blatantly contradict each other. Tip number two? Be proactive, not reactive. Great advice. Tip number three? Go with the flow. Wait, what? Be proactive but go with the flow? Proactively go with the flow? I’m confused.
Finally, there are some definitions and suggestions out there that simply don’t help anyone. Like this little gem:
“To be bold is to laugh in the face of fear. It’s holding your head high as you stride with steadfast stability and purpose. Being bold isn’t just a hobby, it’s a lifestyle and it’s embedded deep within you, you just have to find it and reach in to pull it out.”
So yes, we are talking about being bold—why we should be bold, how we can be bold—but we promise not to give you a quick definition, provide a vague suggestion, and send you on your way. Throughout January, we hope to provide you with examples of what being bold can mean, why it can be a difficult trait to master, and how you can use it to ask better questions. Oh, and we promise, no cliff jumpers.
I could give you the dictionary definition of bold, but you already know what the word bold means. But what do we have in mind when we say we want to be bolder at work? Or we want to be seen as a bold leader? A lot of people say it’s not being afraid of certain things, but I don’t think that’s true. You can be afraid of something and still face it boldly. It really means not letting fear get in the way of certain things.
Someone who is bold does not let fear get in the way of:
It sounds simple enough, but there are a lot of different ways one can speak up at a meeting when they disagree with something, and therein lies the rub. Bold on its own is not always good. I didn’t reference the dictionary definition, but I am going to reference a thesaurus. The word “bold” has three different subheadings in the thesaurus.
We strive for category one. We want to avoid category two. Category three is a bit of a mix. So, if boldness is all of these things, what’s the secret to getting it right?
Behavioral statistician Joseph Folkman said it best in this Forbes article. “The problem with boldness is not the presence of the attribute. It is the absence of the other skills that enable boldness to be helpful.”
In other words, boldness without humility makes you look like an @$$hole. But that’s a rather brash way to explain it. Instead, I could say that I just kind of think we might want to have some humility with our boldness. But that statement had no boldness at all—it was all humility. Instead, I’ll say that in order to be effective, we need to counterbalance boldness with humility. There it is—an equilibrium between bold and humble.
Another way Craig Wortmann of the Kellogg School of Business says we can look at it is a balance between strength and warmth. One of the skills Wortmann says most of us need to work on is figuring out how bold we need to be in specific situations. And then, once we figure it out, balancing that level with the proper amount of humility or warmth.
Like any skill, to get good at it, you have to practice. That means that to be effective at being bold, you can’t just be bold occasionally. You have to be bold consistently. Not only that, but as a bold leader, inclusive marketing leader Sonia Thompson says you should try to build and nurture a culture of boldness. This means that not only are you bold, but you reward your team for bold ideas and actions, and you provide them with opportunities to get out of their comfort zone.
How can sales professionals be bolder? A lot of it does have to do with being uncomfortable, at least at first. One way of being bold is something we’ve written about often—leaning into objections. When objections come to you, address them head-on. Ask more questions about them. Even better, actively uncover objections yourself without waiting for them to pop up unexpectedly.
Another way to be a bolder salesperson is to dig deeper into your prospects’ pain points. In DRIVE, Maestro’s information-gathering framework, part of figuring out the impact your product or service will have is asking not only what problem is being solved, but what will happen if it’s not solved.
If the sale is taking longer than expected or has stalled, a bold salesperson is comfortable digging into a pain point. “You told me that if you don’t improve cybersecurity for your organization, you might lose your job. You also said the solution needed to be in place in the next few weeks. I’m worried about what will happen to you if we don’t get this done.” Sales professionals can provide bold and honest communication because of the foundational work they did building a trusting relationship with the prospect.
One more way sales professionals can be bold is to put forward a mutual plan for themselves and their prospects. After a meeting, for example, it’s appropriate to send an email reviewing what you as the salesperson will do, what the prospect said they would do, the deadlines you agreed on, and any other next steps. Sending such a message is a more direct approach than many are used to, but done tactfully, helps keep the process on track.
We mentioned DRIVE, in which each letter represents two levels of questions sales professionals need to ask to get the information they need. If you’ve read previous blogs, you know how much we love questions at Maestro. From game theory to question trees, much of what we teach is based on how and when to ask questions and which ones to ask. That’s why in next week’s blog we’ll take a closer look at how you can ask bolder questions and how these questions will impact the sales process.
Start your year off right with Maestro workshops for your team. Reach out to us at mastery@maestrogroup.co to schedule.
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