The Value of Taking Risks

The Lead - The Value of Taking Risks

I have a natural tendency towards over-analyzing. Early in my sales career, I would do way too much prospect research before ever reaching out to someone. I’d study their website, scan their LinkedIn etc. looking for some piece of information that would give me the confidence to take action. I’d then spend way too much time trying to craft the perfectly worded email that would instantly grab their attention and get a reply.

At the heart of this tendency, was a fear of rejection, ultimately failure. My deep analysis was a way of convincing myself this was truly someone who could use my services, and by spending so much time in research, I was decreasing the likelihood of failure. A bit silly, no doubt.

That fear can be a killer when it comes to taking action. On some level, I think most people don’t enjoy trying something that doesn’t work. I’ve always admired the folks I’ve worked with who have ironclad skin, and have a propensity for taking risks. It doesn’t come naturally to me. I suspect there are others like me reading this.

As a sales person or sales leader in an organization, it’s one thing if you’re hired to do a job and are handed a playbook. Here’s exactly what we do, here’s how you do it. A lot of people are comfortable in that environnment, and will thrive. But what happens when that doesn’t exist?

The reality is, a lot of small businesses don’t have a cookie cutter system or playbook to run. Being in sales (especially as a team of one) requires a much more entrepreneurial approach vs. simply running a system someone else created for you. Personally, that’s the type of role that gets me fired up. There’s a puzzle to solve, there are opportunities for creativity. It also means, you have to take risks.

The last five months for me have been a good lesson in this, and I suspect it’s just the start. For the purposes of this newsletter, I’ll focus on a couple things related to risk taking when you’re in a business development role. I think this applies to business owners and sales leaders, as well as individual contributors.

Here are some reasons as a sales professional, you should examine your own tolerance for risk, and why I think you should push yourself outside your comfort zone.

You Don’t Know Everything - Sounds simple, but it’s another thing in practice. Here’s what I mean. We all have held beliefs that influence how we see the world. A simple example of this would something like “Cold calling doesn’t work”. You may hold this belief based on experience, or what some guru said on LinkedIn but that doesn’t necessarily make it true. So despite the fact you may have a belief around something’s effectiveness, it’s good to challenge these beliefs from time to time. You may actually surprise yourself. But it’s going to take a step outside what you may be comfortable with. Test your assumptions.

What Works Now, May Not Always - One of the things I see pretty often, is organizations getting comfortable with what’s historically work. Now believe me, I’m a proponent of doing more or what works. It’s easy to get distracted by the shiny object. But there’s also danger relying too heavily on one source or approach for generating opportunities. The best time to test and explore new things, is when it’s not do or die. I think there’s a balance between getting distracted and being laser focused on one thing.

Results Aside, Trying Brings Growth - You’ve heard all the common anecdotes, you miss 100% of the shots you don’t take, we learn more from failure than success. The reality is that comfort can be a trap. If we aren’t trying new things, we put ourselves into a box which makes it even harder to step out. You’re not always going to have success with the risks you take but you will probably learn something. There’s a good chance you will gain confidence, at a minimum that you’re someone who is willing to put yourself in an uncomfortable situation and get through it.

I’ll use a quick example from my own business. I’ve had this idea for a long time that I wanted to run a small cohort of business development professionals in the PM space, focused around developing and executing an outbound strategy. For months, I kicked around the idea, the format, the content, and what I might charge. But I kept coming back to, is someone actually going to want to do a program like this?

I didn’t feel like I had enough information to launch something like this without feedback from the market. I felt stuck. Until one day I decided to reach out to my network and form a test group. I didn’t charge this group anything, only asked that they commit to participating and offering feedback.

We ran this group for six weeks. Overall, I’d say it was a sucess. I learned a lot, and was given some great feedback on what worked and what didn’t. In some ways, I reduced the risk for the participants because I didn’t charge them anything. But, I still carried risk on my side by putting myself, and the content out there. I spent a lot of my own time creating and refining something to share with others.

Ultimately I came away with what I hoped for, which was some proof of concept and feedback from the market. Now the next risk will be launching something out into the world. Taking this initial leap though, got me closer to that point and taught me several things.

If you’re a sales person or leader who feels stuck, I’d challenge you to think creatively about where you may need to step outside your comfort zone. Is there some idea you’ve been kicking the can on? Get off the sidelines and take action. I think if you’re feeling comfortable, that’s actually the more dangerous place to be. Unlike the stuck person, you may not have a sense of urgency to experiment. Maybe ask yourself this question - if everything I’m doing today suddenly didn’t produce results, where would I go from here?

As always, I hope this has been helpful and thought provoking for you. Thanks again for subscribing!