Category: Leadership

One of the challenges we always had with software engineering was finding the balance between strict deadlines and time to get it right. Software development is still more art than science, especially when innovating and working on major changes. Different constituents like customers, prospects, analysts, sales, support, and engineering have things they’d like to see, and want visibility into when the features will be delivered. Naturally, the market changes so fast that as an entrepreneur or product manager, there’s a desire to push back on too many fixed deadlines as that limits flexibility to adapt to new information.

Here are a few considerations with balancing software engineering deadlines:

• Work off short deadlines, like two week sprints, and use that to keep up a good pace of progress (don’t allow any to do items longer than two weeks such that something that might take two months is broken down into two week chunks)
• For longer range considerations and road maps, try painting broader strokes for areas that will be addressed instead of specific improvements
• Find a level of accountability for the engineering team such that there’s ownership over delivering on time while also making sure it’s fully baked (don’t let the balance of influence sway too much such that deadlines and deliverables aren’t met while still being realistic)

The best thing to do is to build a really strong engineering culture that views code as craft and has peer-to-peer accountability.

What else? What are some other considerations for maintaining a software engineering balance between strict deadlines and time to get it right?

One of the questions I get from entrepreneurs is “how has your day-to-day changed going from a seed stage startup to a growth stage startup?” The three core responsibilities of a CEO never change: make sure there’s enough cash to keep going, help set the vision, and get the right employees on board. For my first year as a seed stage CEO, I spent most of my time writing code (~40 hours/week) and the rest of the time doing whatever it takes to be successful (20 – 30 hours/week). Now, five years later, things are much different.

Here’s what a typical day looks like:

• 10 minute daily check-in with the executive team
• One or two one hour catch ups with a department head (meet with each department head bi-weekly)
• One to two hours working on strategic projects (usually juggling 2-3 strategic projects at any one time)
• One hour reading blog posts and books (usually read one business book per month)
• Miscellaneous meetings, email, and other work

As you can see, the ratio of doing front-line work to managing people changes dramatically as the startup gets larger. Days go quickly and are very productive.

What else? What does a day in the life of your startup look like?

Recently I started reading the book Difficult Conversations: How to Discuss What Matters Most by Douglas Stone, Bruce Patton, and Sheila Heen. The authors are a research team at Harvard working on the Harvard Negotiation Project, which has been in the works for several decades. In all aspect of life, and especially the startup world, as with any fast-paced leadership situation, there are a number of difficult conversations with team members, customers, investors, and more.

One of the areas that resonated with me was around why we each see the world differently and how to better understand another person. From the book, here are three reasons why we see the world differently:

1. We have different information
   – We notice different things
   – We each know ourselves better than anyone else case
2. We have different interpretations
   – We are influenced by past experiences
   – We apply different implicit rules
3. Our conclusions reflect self interest

If you’re looking for advice and guidance on being a better leader and communicator, this book is for you.

What else? What were some other takeaways from the book for you?

One of the most popular self-help and professional development books available is Dale Carnegie’s How to Win Friends & Influence People. Amazingly, the book was published in 1936 and is still supremely relevant today. As part of our leadership development program, we’re doing a book club with this being the next book on our list.

For leaders, the book is a must read. Yes, it is commonsense but commonsense that needs to be thought through and digested on a regular basis. Leaders are more effective when they are liked and respected — team members generally want to work for, and with, people they like.

From the book, here are six ways to get people to like you:

• Become genuinely interested in other people
• Smile
• Remember that a person’s name is to that person the sweetest and most important sound in any language.
• Be good listener. Encourage others to talk about themselves.
• Talk in terms of the other person’s interests.
• Make the other person feel important — and do it sincerely.

How to Win Friends & Influence People should be on the list for all entrepreneurs and leaders looking to get better at what they do and how they do it.

What else? What are some other ways to get people to like you?

One of my favorite quotes is “A good plan, violently executed now, is better than a perfect plan next week.” by George S. Patton. Now, just because one plan is good, but not perfect, doesn’t mean that the management team isn’t aligned and on the same page. One of the mistakes I’ve made several times is worked on a plan with my colleagues, solicited input, and pronounced it good enough to execute. Only, everyone else wasn’t on board — management wasn’t aligned.

Here are some ideas to develop management alignment in startups:

• Balance input in person, phone, IM, and email without relying on just one digital medium
• Articulate the plan in the simplest format possible, preferably a one page Google Doc with bullet points
• Ensure key stakeholders have seen the plan and voiced their opinion
• Consider a consensus-driven approach or a leader-decided approach when ready to execute

The harder the plan, the harder the management alignement. Following these ideas makes the management alignment process easier.

What else? What are some other ideas to develop management alignment in startups?

Recently I started reading the book Wooden on Leadership after a recommendation from a colleague. The book’s author, John Wooden, is one of the most successful college basketball coaches ever and an amazing leader. In the book, Wooden describes his pyramid of success that he developed over the years:

• Competitive Greatness
• Poise | Confidence
• Condition | Skill | Team Spirit
• Self-Control | Alertness | Initiative | Intentness
• Industrious-ness | Friendship | Loyalty | Cooperation | Enthusiasm

Startups defining their core values would do well to use one or two items from Wooden’s Pyramid of Success (I’m a fan of no more than 3-5 core values otherwise there are too many remember). For entrepreneurs interested in the leadership and the study of leadership, I’d recommend the book.

What else? What are your thoughts on John Wooden’s Pyramid of Success?