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20 Leadership Things Learned in 20 Years

This month marks the 20th Anniversary for Warren Douglas Advertising. In reflection of my experience over the past two decades, here are 20 of the most significant leadership lessons I’ve learned while working with our incredibly talented group. Admittedly, some of these concepts are principles taught to me by other leaders, mentors, and YPO colleagues, but I’m still learning and applying all of them on a regular basis.

  1. Leadership is harder than it looks—The need to influence others when they may not understand my perspective has proven to be one of the toughest challenges of my career.
  2. People need connection—Yes, we’re running a business, but output and productivity increase significantly when people are personally connected and when they know they’re genuinely cared for.
  3. Success isn’t guaranteed—Just because last year was great doesn’t mean that this year is a shoe-in, and what worked in the past may not work in the future.
  4. The problem is in the mirror—If I see a problem, and I wait for someone else to solve it, I actually become part of the problem. So in an ironic way, the solution is in the mirror, too.
  5. Never say “never”—This attitude is a sure way to make a liar out of yourself. One can’t know today what tomorrow might hold.
  6. Innovate or die—We’re all seeing this truth become reality in industries we interact with daily, from how we buy groceries to how we watch movies. An incessant appetite for innovation is now table stakes for any viable business.
  7. Keep emotions off the table—When dealing with conflict, wearing my feelings on my sleeve bites me back every time; a cool-headed, facts-first approach shows me that feelings often misguide me.
  8. Differentiation requires courage—If I hear another client tell me that “our people and our customer service are what make us different,” I think I’ll choke. It is truly difficult to be different, especially if there are lots of competitors in your field. The advertising industry is no exception.
  9. Clarity and redundancy feel the same—Just because I said it once doesn’t mean people understood it. (Anyone with kids knows this!) Many times the messaging repetition concepts that work in advertising also apply to organizational communication.
  10. Problems don’t get better with age—I have to give credit here to my friend, Jim Blackburn, for this phraseology. Leaders have to lean into problems, not avoid them. The hope that they’ll just go away is a fast track to things going wrong on your watch.
  11. The honeymoon lasts six months—Hiring a new person is always somewhat of a risk. I’ve seen that it takes six months to see their true colors. People always try to impress in the interview process, but by month six, a manager can see if the performance and behavior match up to the expectations set during the hiring process.
  12. Mediocrity is expensive—The cost of team members who don’t deliver excellence can create a cultural and financial hole that’s difficult to dig out of.
  13. Leadership requires practice—Good leadership doesn’t just happen organically. If there’s not deliberate effort toward leadership awareness, a good culture deteriorates.
  14. Managing growth is easy, managing smaller is hard—Knowing when and where to cut expenses is emotional and painful. It’s much more fun to count the cash coming in, spend money, and hire more people.
  15. Risk and reward are close relatives—It’s not common for great reward to come without having made some gutsy moves. Wisdom and a lot of prayer are necessary to know what risk is worth it, which leads to my next nugget of insight.
  16. The line between faith and foolishness is thin—I’ve second-guessed myself so many times, thinking that our new ideas and approaches were either brilliant or insane. The risk that can come with doing courageous things can be tough to evaluate objectively.
  17. If you’re not growing, you’re dying—Professional growth should be constant. If I’m doing things the same way today that I did three years ago, I could be losing momentum. I’ve discovered that it’s worth spending some time to question whether or not my professional routine is changing enough.
  18. People need to know how important they are—It’s a game changer when team members understand how important their role is to the success to the organization. It’s highly complex, however, to articulate company, team, and individual goals in a way that is clear and measurable.
  19. Don’t forget the family—The long hours and stressful dedication required by high-performance teams comes at a cost to the spouses and loved ones who support them. Including significant others to company celebrations lets them know that their support is appreciated.
  20. Kill them with kindness—Treating people with generosity and thoughtfulness—even when it seems they don’t deserve it—has always served our company well. It’s encouraging to see others in our organization adopt the same philosophy, extending it to clients, suppliers, and colleagues who may not be having their best day.

Stay tuned as I dive a little deeper into each one of these concepts in future posts. I’m certainly no master at any of them, but I’m constantly amazed at how much better organizations perform when good leadership principles pervade the culture.

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