Hassan Osman is the Program Management Office (PMO) Director at Cisco Systems, where he leads virtual teams on delivering large and complex programs for our strategic customers in the Americas region. He previously worked as a management consultant at Ernst & Young (now EY) where he spent his time analyzing troubled programs at Fortune 100 companies and recommending strategic plans to improve their alignment with project objectives. Osman is also an author who has written several books including Influencing Virtual Teams and Don’t Reply All.

Where did you grow up and what was your childhood like? Did you have any particular experiences/stories that shaped your adult life?

I’m originally Lebanese, but I grew up in Abu Dhabi, UAE. My family moved there to avoid the Lebanese Civil War at the time. I was fortunate to have a stable childhood and loving parents. I attended an international school, where I mingled with students from many different cultures and backgrounds at an early age. Those interactions with diverse kids helped me become more empathetic to people as an adult.

What is something you wish you would’ve realized earlier in your life?

That 80% is good enough. I’m a perfectionist by nature, and that trait has been crippling for most of my early years. I used to wait for near-perfect information before moving forward, but if I knew that 80% would suffice, I think I would have failed more often and learned at a much faster pace.

What are bad recommendations you hear in your profession or area of expertise?

That you should focus on one thing at a time. This probably sounds counter-intuitive and against general advice, but I think that managing your distractions, instead of trying to halt them completely keeps you engaged and increases your overall satisfaction. This applies at the macro-level, such as having a side gig or pursuing graduate studies while working a full-time job, and at the micro-level, such as multitasking on a couple of activities while trying to execute on a primary one.

What is one thing that you do that you feel has been the biggest contributor to your success so far?

I think if I were to pick one contributing factor, it would be having a general sense of curiosity about the different subjects I’m interested in. I ask a lot of questions to try to understand why things work in addition to how they work. I’m inquisitive by nature, and I think that has helped me learn and grow in both my professional and writing careers. The other is overcoming the stigma associated with failing. I think it’s super hard for anyone to be successful if they fear failing in public.

What is your morning routine?

I wake up at around 6:00 or 6:30 am and do everything sane people are not supposed to do.

While still in bed, I check my phone for notifications and emails. I respond to any urgent fires. I then read through social media accounts and news headlines to find out what’s going on globally.

After around 30 minutes or so of useless scrolling, I hop out of bed, brush my teeth, and then make myself a cup of coffee (usually black, but if I feel like getting out of the house, my go-to drink is a hot latte with almond milk from Dunkin Donuts).

I then log on to my PC and start my day by addressing emails before jumping into any early morning meetings.

What habit or behavior that you have pursued for a few years has most improved your life?

Listening to the signals that my mind or body is sending me. I used to plow through any procrastination or lethargic signs to get things done, but that wasn’t productive over the long run. Over time, I learned that if I’m feeling lazy or sluggish, those were legitimate signals that I had to just stop what I’m doing and focus on something else that interests me. Overall, that has made me happier in the long run.

What are your strategies for being productive and using your time most efficiently?

I follow concepts from two books. To improve effectiveness, I use many ideas from Tim Ferriss’ classic, “The 4-Hour Workweek.” And to improve efficiency, I follow the lessons from David Allen’s bestseller, “Getting Things Done.”

What book(s) have influenced your life the most? Why?

I’m a big Malcolm Gladwell fan, and all his books, including “The Tipping Point” and “Blink” combine masterful storytelling and detailed research analysis to address a specific theme. I write short books for busy managers, and Gladwell’s books have significantly improved my writing craft. Most importantly, his work has helped me understand the importance of telling great stories to keep readers engaged.

Do you have any quotes you live by or think of often?

“Family Always First. Keep Learning. Keep Grinding.”

Those are seven words I had to choose for a leadership program I attended a few years ago and they pretty much sum up my philosophy on life. The words hang above my office desk and represent my North Star on every significant decision.