One of the biggest learning lessons I’ve had in my business career came after I was fired for the first time in my life. At 23 years old I was the 5th person to join a start-up that a few friends of mine from high school started. We were self- funded and had no idea what we were doing but were more driven than most to succeed. We ended up being the fastest growing company in Massachusetts for 3 years in a row, getting up to 85 employees and $12M in revenue. After 7 years the Mergers & Acquistions market started to heat up and we looked to sell the business. Staples came into the picture and became the leading contender to purchase us, which they ultimately did.

During their evaluation process, Staples wanted to interview each of the executive team members to get a feel for us, how we ran the business and what we felt about the acquisition. I remember being in a management meeting where we talked about how we needed to make sure we were all on the same page and didn’t say anything that would jeopardize the sale. We even worked with a consultant to come up with the potential questions they might ask and practiced our responses to each.

The head of Staples’ contract division (a $12B part of the business) was the one leading the interviews. He met with each of us individually and asked us a variety of questions. I remember feeling rather awkward answering the questions with the scripted answers we came up with as a group. If anyone knows me, they know I’m about as transparent as it gets which means I’m not a very good liar. Needless to say, after the interviews my CEO met with them for feedback and the feedback was good across the board for everyone except me. They told my CEO that I “wasn’t the right guy for the job” which blew my CEO away since he felt that if anyone was the guy it would have been me. I was the heart and soul of the company culture and bled the company colors. My CEO fought for me and I stayed on board without knowing I was destined for failure.

The next year was filled with turmoil as I tried to fit into their corporate culture and figure out how to drive results while dealing with bullshit, internal politics. It didn’t matter what I did, it almost always backfired on me and made me look bad. While going through this painful process I had this nagging desire to reach out to the main guy who I was told didn’t like me and have a real, rather than scripted conversation with him. I thought if I could just grab a beer with him we would have a better understanding of each other. Unfortunately my CEO, with all good intentions, discouraged this as he was concerned I would say something that would get me fired.

About one year after the acquisition, my CEO came into my office and told me they were going to hire another VP of Sales and wanted me to transition out over the next few months. They effectively fired me. I was devastated. It took me a long time to come to grips with it. After my final day, I was feeling good about the next stage of my career but that initial interview and my relationship with the head guy was nagging at me. So, I reached out to him directly and asked for an hour of his time to answer some questions I had for my own personal and professional development. He was overly accommodating and more than open to meeting with me, telling me that mentoring young leaders was one of his favorite things to do.

That was one of the best hours I’ve ever spent in business. He answered all my questions and more. There was one answer that stuck out and changed my perspective on a lot of things. I asked him if he would have been open to a candid meeting like this when I was working for him. He seemed perplexed and asked why I thought he wouldn’t have been. I explained that I was told not to reach out to him by my CEO who felt that I would have said something to jeopardize my career. His response has stuck with me ever since. He said – “what’s the risk?”

I thought about the question for a little while and then explained that the risk was me getting fired and disappointing many of the people who were relying on me. He then gave me two scenarios. In scenario one he asked – if you had gone over your CEO’s head and came to me to have a discussion like this and I got pissed and told your CEO about it – would you have wanted to work for me regardless? My answer was ‘no.’ He then highlighted how I would have figured it out much earlier in the relationship and probably not had to spend a year getting my ass kicked and having it end like it did. For scenario two he asked – say you went over your CEO’s head and we had a really good conversation like this – do you think we would have had a much better working relationship and you would have been more successful over the past year? My answer was an obvious ‘yes.’ With that he asked again – so what’s the risk?

He was right, the risk was actually doing what I did and not being true to myself or speaking up for what I felt was right. Ever since then, when faced with a decision on whether or not I should speak up about something I believe in, I ask myself – what’s the risk? If my intent is genuine and focused on doing good then the risk is ultimately quite limited from a big picture standpoint. I apply this now to all aspects of sales, business and life. Some examples as it relates to sales: going over someone’s head; pushing back on the customer when I think they’re making a poor decision or looking at things the wrong way; respectfully challenging my manager when I don’t agree with a certain direction; trying a different approach to a common objection. There are tons more examples but my hope is with this post you think about the challenges you’re facing in your career and ask yourself – what’s the risk? and do what you think is right.

#Makeithappen!

John Barrows has held every position in Sales including inside, field, channel, executive management and ownership. He continues to sell every day using the techniques he trains to some of the world’s leading tech companies including Linkedin, Marketo, HP and most notably Salesforce.com. He has worked with Salesforce.com for over 5 years and trained over 3000 SRs, EBRs and AEs on techniques that have driven millions of dollars into the pipeline.