One of my friends runs a back-office operations firm and was recently approached by a software vendor who wanted her company to become the country’s reseller for their software. She asked me how I’d go about making that business decision. I wrote up this set of questions to help her think things through.

Photo by Markus Spiske on Unsplash


Market Size and Market Fit

How big an opportunity is this?

One of my friends recently landed a new senior management job. We got together over coffee one weekend to brainstorm what he should do to start strong in his new role. This post is a sanitized summary of our discussion. I hope you’ll find ideas in this post that you can pick up and apply immediately.

Photo by David Iskander via Unsplash

Ask these questions at your first 1:1 meeting

The most important meeting in your first week at a new management job is a 1:1 conversation with your new boss. Reserve at least 45 minutes, preferably an hour, for this first meeting. …

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When you’re working on a project with a team, department, or company for the first time, there are nuances and political undercurrents unique to your new organization that won’t be immediately obvious to you.

To avoid potential blunders, meet with your project sponsor and key colleagues to ask specific, probing, and open-ended questions to help you get your bearings. Below are some questions to get you started.

1. What’s my top risk?

Given what you know of sprints / products / projects / task forces / initiatives / implementations that the company has undertaken in the past, what do you think is the single biggest…

I just spent a week in Hong Kong, and thanks to some great advice online, I had decided to bring one of my Airport Express devices with me in the hopes that I can get my Google Chromecast device to work on it.

I had stayed at the Park Lane Hotel in Causeway Bay (which incidentally has a nicely appointed hotel room for Persons With Disabilities — including a roll-in shower and grab bars around the toilet). …

Lessons from My Favorite Mentor, Part 2

Delegating is like tossing a ball and expecting the other party to catch.

My favorite mentor liked to explain the concept of Delegating through the metaphor of teaching kids how to catch a ball.

When you play catch with a very young child, you ask them to open their hands, place the ball gently into their cupped palms, and wait for their fingers to curl around the ball.

As the child gets older, you can now hold the ball a few inches above their hands, then drop the ball for them to catch.

With a 5-year-old child, you can easily toss the ball from a few…

Image credit: Nabeel Syed

It was the year 2000. I was thirty years old and four years into a job with a boutique consulting firm. I had high-pressure days which began with a 1.5-hour drive to the client’s office and ended with a 2-hour drive home.

It was the year audiobooks and Leo Laporte’s podcasts saved my sanity, and my attempts to learn Instant Italian by CD kept me amused on my solitary commutes. …

Two years and three clans later, it dawned on me that leading a clan is exactly like leading a team

If you’re reading this, there’s a good chance you’ve seen or heard of Clash of Clans, the top-grossing game for iOS and Android from Supercell.

It occurred to me today that leading a clan is a lot like leading a team at work. In fact, I would go so far as to say that the same set of leadership principles can be applied both at work and at play. This post is my attempt to explain why.

A quick disclaimer: while I’ve tried to make this post useful even for non-players, you’ll get a…

Five Ways to Ensure Your Point Still Gets Across

Let’s face it. Everyone is busy these days and there are too many things competing for your readers’ attention, especially in the workplace.

On a daily basis, we are inundated by emails, slide decks, proposals, product briefs, design documents, status reports, policy papers, news, and more.

Readers skim because they lack time

When people do not have enough time to read, much less think, what do they do? They skim. And, let’s admit it: so do we.

In fact, skimming is such a popular coping mechanism that there is no shortage of articles and books that teach people how to master skimming…

Congratulations! In recognition of your excellent performance, your passion for the job, and your professional aspirations, you’ve just been promoted to team leader.

I’ve been there myself and I know all too well the cocktail of emotions that you feel right now: pride in your accomplishment, excitement at this chance to prove yourself in a new arena, and nervousness about how well your former peers will accept your leadership.

In this post, I will share with you the book that helped me the most when I was at this stage in my professional career, in the hope that it will…

Lessons from My Favorite Mentor, Part 1

In the past two and a half decades, I’ve had really great mentors at different stages of my professional life. One mentor, however, remains my favorite. He was my CEO at a previous job and he had a way of using picturesque turns of phrase to express himself. He also didn’t mince words; you always knew where you stood with him.

While my mentor has since retired from consulting work, his quirky lines still remain with me. In fact, I find myself muttering some of his lines now and again — as recently as last week.


Always curious about Business, Tech & Startups, Leadership & Management, Writing & Editing, Life. You can reach me through DMs on Twitter at @mdy

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