Category Archives: Operations Leadership

The Hardest Skill To Master – Empathy

Empathy and EncouragementAny growing venture is hard. My last three years have been at an incredible pace with days blurring into weeks and months. It does not have to be a startup, it could be a lifestyle business, it could be a mid-size business. The faster the growth, the more extreme are the swings and tensions. It is way too easy to lose sight of what matters, end up with agenda, and kill your relationship.

So how do we survive and thrive?

It all starts with empathy. The more the person you should be supporting is different, the harder it is for you to relate and understand where the other person stands. You are ineffective without the empathy. So you must try to gain understanding about what is affecting your colleague. Maybe something in personal life is bothering them, or they are at the edge of their wits at work, or maybe there was a string of setbacks or lack of progress, etc. You have to care about their pain to be effective. There will be a day you will need their empathy.

What you may think are variables within their control, might not be the case at all. Let me use sales as an example. There are certain times in the year (usually clustered around holidays) when hitting those sales numbers might be much more challenging. Even the best seasonality models are off almost all the time. You thinking that if this person “makes the calls and will make the sales” may make sense during your typical month, but not when the school is out, or storm screwed up daycare plans, or market developed some macroeconomic fears. Understand and embrace that. Then you may end up with a much clearer view of what can this person affect and that is where your help and motivation are most valuable.

Create new options instead of poking holes. I know I sometimes really stumble on this, being extremely pragmatic. Criticizing is the easiest option with highest social cost. You can insert your opinion until your face is blue and do nothing but waste time and cause further demotivation. Likely, if this person knows their craft, they already introspected and are dealing with the issues. To be most effective, you have to create new options. Think of new concrete suggestions you can provide. Maybe this person was so in the weeds, they weren’t able to see that one additional option you noticed. Be generous with help. You may not always get the credit, but you will always gain appreciation. At the end of the day, having someone to go to, when you are stuck, is invaluable.

Dismount that “high horse”. The biggest fallacy is to assume the other person has an easy problem. Likely that is just an opinion not based on actually doing the job. And if you think the problem is easy, get off your high horse and get your hands dirty. You don’t get to say “that is an easy problem to fix,” one doing the job is the only one entitled to make the statement. Either help do the job or move along.

Look for wins other person is not seeing. If you ever read the “The Progress Principle,” you know how important it is to recognize even small milestones/wins. Recognition breeds motivation. When you are “in the weeds”, you lose sight of your wins, because survival instincts kick in.
Conflicts are not inevitable. Conflict, at times, is good between people who respect and value each other. But in the end, if you are in the same battle together, compassion goes a long way

Myths Why Startups Don’t Need COOs and Operations Executives

As my regular readers know, I am a startup operations veteran with “battle scars” from 9 startups (co-founder in 2 and early employee in most). I have acquired a PhD in operations from the school of hard knocks after years of being around some very smart people and working on difficult problems. Today, I am… Continue Reading

What Do Operations People Do?

Your operations people are the reason customers are happy, vendors continue providing you with services, and employees have enough resources. Operations team is the “A-team” of vision logistics and their #1 mission is to take care of the organization (feed it, protect it, and maintain it). Not all small companies and startups have operations teams,… Continue Reading

Being a CEO Is a Brutal and Lonely Job, But It Doesn’t Have To Be

Who gets their head “chopped” if a company can’t get traction, hit their sales numbers, find enough financing, or retain their high-performers? Who has to be the chief recruiter, fundraiser, strategist, and often makes the most expensive mistakes? Who has to listen to endless opinions and filter out all that noise? The answer is simple –… Continue Reading

Building Compensation Package: Startup Equity Compensation Framework 2.0

Let me start by saying that building a total compensation package is HARD! This is an extremely important component of business planning, but many executives end up “winging” it. Instead of taking time to do the math and some modeling, we just slap something together and pray our compensation structure won’t crumble. For me personally,… Continue Reading

What To Look For In a Chief Right Hand Person (COO, VP of Operations)

Last week a founder of a software development company asked what to look for in a COO on Since this is a fairly common question to me, I decided to expand upon the answer I posted and further describe what attributes a great business operations leader/professional should possess. Bit of background: I have been… Continue Reading

How a Foosball Table Can Kill Your Startup – part 2

Since an article I wrote in June of 2009 called “How a foosball table can kill your startup” is still sparking attention and conversation, I think the time is ripe for me to expand on the topic. Yes, I still believe that tchotchke “benefits” do nothing but waste money.  Instead, use your resources to attract… Continue Reading

How To Create a Non-Disclosure Agreement People Can Understand

Like many of you in the startup world, I have read and signed my share of non-disclosure agreements (NDAs). I have reviewed, edited, and sent hundreds of them in my career, but I am yet to come across one that really serves anyone but the lawyers who charged dearly to write it. So, why don’t… Continue Reading

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