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I’m ashamed to admit it, but it took me awhile to figure out that it is okay in business to stand up for yourself. I grew up in a blue-collar home. You traded time for money and clocked out at the end of the shift each day. Forman who had earned the title by seniority from grinding it out had authority and power over whether you family had food on the table.

I’ve taken a different path for my career in software and technology. I’ve never regretted a moment of it in my lifetime–sleepless nights or not.

“Are you “effing” listening to me?!?! Are you?!?” (This common monolog went on for several more minutes with several colourful expletives aimed at me and my character from the CEO–that’s how he chose to lead or he was always having a bad day at home or the office. Either way, it is inexcusable in any business setting.)

I responded, “Yes, I’m listening, but I don’t think you understand. I’ve done a thorough analysis of the order and revenue information. The numbers are correct.” I was not backing down because of his usurpation of power. I knew I was correct because I lived in the numbers daily, but that was not good enough for them–they had already played their “cards” that day. I can admit I’m wrong. Today I was not, but that did not matter.

Let’s just say that we both grew weary of being confident in our positions on the state of the sales for the quarter, the projections, and honestly, he probably got tired of yelling at me because I did not cower away and back down. I was sick of dancing around it too.

The Price of Porcelain

After the meeting was over, my boss at the time asked me if I was okay? “Of course, I was alright.” I was more concerned that my boss thought I was porcelain. I don’t crack that easy.

What did that say about how my boss viewed me? In my eyes, I was earning the respect of our leader through the interaction by holding my ground. I tend to be quiet and reserved, but confident when I speak. I learned that being too quiet apparently equals weakness in some eyes.

I’ve heard others talk to hear themselves speak in other product leadership settings. I’m convinced that they have received some bad advice somewhere. Don’t do it. Please. Agile applies to the art of the spoken word as well.

Confident, but not Cocky

Okay, my exceptional product leaders friends I have a question for you. How do you demonstrate self-assurance without being excessive in your approach? As I see it, confidence is something we earn over time, whereas cockiness we delude in our mind.

Confidence requires time
Cockiness deludes minds

I’ve heard it explained another way as well–the above is mine. Confidence comes from our ability to pick ourselves back up after we keep getting knocked down. Makes sense, right?

What you should understand is that we are going to get knocked down as software product leaders. Something as fragile as self-assurance is always at risk of market forces. Someone will always be trying to unseat us from our positions in the marketplace. What is even worse is the risk we have within the four walls of our business.

In his book the Power of Habit, Charles Duhigg talks about the delicate balance of institutional habits. Everyone understands that the organization survives on profits. We can’t give significant discounts on our product at the expense of profitability, or everyone will be looking for employment. Balance must exist within these ego-driven fiefdoms.

A master product manager understands their role in the organization. They can project confidence to the team with the information that is available at the time–whether a little or a lot. But overconfidence can get you killed. It is a balance.

To quote Ice Cube, “Check yourself, before you wreck yourself.”

As I close, I would not recommend picking verbal fights within your organization with anyone–it’s not productive. If you do find yourself in a situation like mine where the leader of the herd needs to lock horns once in a while to exert their dominance, it is best to engage with confidence. Confidence trumps cowardliness.

If you are wondering how it all turned out for me with my CEO, our business relationship blossomed from that point forward. I went on to have a long, successful career working in their organization. The lessons I learned about myself and the confidence that I gained have helped me every step of the way in my roles as a Product Leader.

Please share your experiences below in the comment section about when you have had to choose between leading with confidence (or cowardliness–no judgment here because I have had my share of both).

Brian Stout

Senior Software Product Leader


Star Product Leader PSA

The team at Pragmatic Marketing created an incredible infographic that gets to the essence of what skills a “rock star” product manager or product marketer are likely to possess. You must check it out here. Print it. Make it your wallpaper. Pin it up on your wall. Frame it. It is that good.

I’ve been a software product manager for many years now and lead some exceptional teams. I’ve seen these traits in the best product leaders (and humbled when others have seen them in me) and will share some insights I have found on how you enrich these individuals and help make your teams even better.

I’m building on the nine traits as defined by Pragmatic Marketing of Rockstar Product Leaders at the links below:
(Please give them some love and get certified–it’s worth the investment)
1. Curiosity (Turn Up Your Rock Star Product Leaders)
2. Charisma (Take Notice: The Charismatic are NOT Static)
3. Competitiveness (Better Than You: Competing for Product Leadership)
4. Optimism (Look on the Bright Side: Ludicrous Mode for Product Leaders)
5. Servant Leadership (In the Lead: Servant Leadership)
6. Confidence (“Yes, I’m Listening”: How Confidence Trumps Cowardliness)
7. Integrity (Getting High: How Lofty Integrity Lifts Products)
8. Whole Person
9. Always Learning Expert
10. The Missing Trait