This updated post is being re-published while the author is in the middle of an international vacation—a topic in keeping with the theme of this week’s entry.
We’re focused on being bold, which honestly has me a little bit nervous. Why? I’ll be bold right now and tell you—a lot of stuff on the internet about being a bolder person is trash. First of all, there are way too many images of people jumping out of planes and scaling cliffs. You shouldn’t 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 for how you should 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.”
- This sounds like it’s going to get very messy, and
- I like alliteration as much as the next guy, but I have never stridden with steadfast stability anywhere. What does that even mean?
So yes, we are talking about being bold—why we should be bold, how we can be bold—but we promise more than a quick definition and a vague suggestion, before we send you on your way. We’ll be bold, and provide clear examples of what that 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.
WHAT IS BEING BOLD?
I could give you the dictionary definition of bold, but you already know what the word means. But what do we mean when we say we want to be bolder at work? Or do we want to be seen as a bold leader? A lot of people say it’s being unafraid 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 bold does not let fear get in the way of:
- Trying something new
- Asking difficult, but necessary questions
- Being honest
- Admitting when they need help
- Admitting when they’re wrong
- Accepting feedback and criticism
- Leaving their comfort zone
- Providing others the opportunity to leave their comfort zone
- Speaking up when nobody else does
- Asking for what they want
It all sounds simple enough, but there are hidden complications. You can speak up at a meeting when you disagree with something, and therein lies the rub. Bold on its own is not always good. Bold on its own can get you fired.
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.
- Adventurous, brave, daring, fearless, resolute
- Audacious, brash, brazen, insolent
- Bright, colorful, flashy, loud
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?
BOLDNESS CANNOT STAND ALONE
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.”
Boldness without humility makes you look like an @$hole. But that’s a brash way to explain it. Instead, I could say that I just kind of think that maybe we might want to have some humility with our boldness. But that statement has no boldness at all—it’s all humility. Instead, I’ll say that 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, we balance 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 guru Sonia Thompson says you should try to build and nurture a culture of boldness. This means not only that you are bold, but also that you reward your team for bold ideas and actions and provide them with opportunities to get out of their comfort zone.
BEING BOLD IN SALES
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, impact is the central pillar on which the rest of the structure relies. It’s so critical because measuring the impact your product or service will have is not only asking what problem is being solved, but what will happen if it isn’t.
If a 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.”
In the presence of trust, sales professionals can communicate boldly and honestly because of the foundational work they did in building their relationship with the prospect.
Another way sales professionals can be bold is to offer 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, it helps preserve velocity.
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.
Asking questions is critical to uncover what you don’t know—and to correct what you’re wrong about. Cognitive bias—on either side of the call—can cost you rapport, velocity, and ultimately the deal. You can read part one of our new four-part series about different aspects of cognitive bias, and be sure to come back next week for the second installment.
Have a bold plan, but need advice on how to execute your masterstroke safely? Reach out to us at mastery@maestrogroup.co so we can help you make your next big move.