On Sudden Losses

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Without going into too much detail, we lost one of our dogs in a freak accident recently. My wife and I were out on a date when we got the call from the emergency room.

It’s a highly emotional moment for both of us when something like this happens – especially when it’s sudden. For folks that know us well, our dogs are our children. We know each of their personalities, quirks, mannerisms, barks, and even their barking styles and what they mean. Sure, call us crazy and maybe we are, but the love we have for these dogs transcends just a simple relationship.

It’s hard to describe the range of emotions that one can go through when something like this happens. We all cope differently. My wife does it all at once. I tend to chunk my grief into stages and spread it out to ease the pain. There’s no one way to cope with a sudden loss of someone you love.

It’s a cliche saying but make every moment count. I was putting on my shoes in the morning when our lost dog came and nudge me to scratch her neck. That was my last memory. For my wife, hers was cutting her nails, grooming her hair, and giving her a kiss on the nose. You never know when something tragic will strike. I don’t think it’s reasonable to always live like tomorrow won’t come, but I do think I’m realizing it’s becoming more important to take more frequent moments to appreciate the things in life that you have – especially those around you that support you (whether human or animal).

We tend to ignore them because we’re too busy with our lives, focusing on what we perceive is “important”. Money, jobs, politics, news, whatever. At the end of the day, we all die. When we die, the moments we remember that create a foundation and central tenancy for who we are is what we will remember. I believe those moments are often reaffirmed and hardened through deep emotional connections with those that support us through thick and thin.

There’s a great quote that we have on a painting in our kitchen: Dogs are not our whole lives, but they make our lives whole.

You were way too young to go. We’re sorry we couldn’t protect you. I hope you know that we love you very much and that you mean the world to us. I hope there’s a lot of giant fields in dog heaven for you to play in. We’ll miss you, Eve, and I hope you forgive us.


Companies Lie To Themselves

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I have a bone to pick. Having worked for a decent amount of enterprise focused software companies now, I’ve determined something that truly bothers me. I think this may be very specific to software (perhaps not though!).

Companies are constantly lying to themselves – and it’s making them worse.

I mean this in particular towards the sales and product teams. I understand why they do it but I disagree with the entire premise. Here’s how it goes.

We’re in a competitive deal. There’s multiple other potential vendor plays. It’s the final stages of the deal and BAM! The champion delivers the email no sales person wants to hear: “We went with another solution”. The org starts freaking out, tries to save it, but ultimately can’t. We send in competitive research to do a post-mortem and figure out what happened. Then, we send out an email to the broader organization, generally saying something like the following:

  • “They weren’t the right market fit size for us”
  • “They didn’t have enough budget and we were too expensive for them”
  • “They aren’t mature enough yet for our solution”

Here’s what I don’t like about the above: none of it comes back on the company. It often times feels like we pass the buck on why things didn’t go well. While statements may be true, there is significant product development feedback in each of those quotes.

In a little bit of a rant, what I hate about it is it creates a culture of “us vs. the customer”. Teams read through the emails and don’t view it from the lens of how we, as a company, can do better. Where we can improve on in the product, whether our pricing structure makes sense, whether our product messaging is hitting the right audience, whether it’s easy enough for users to use our product, and so on. We say things like “well, guess that customer is going to miss out on how awesome we are”.

It’s that bravado that drives me nuts. Part of building software is the relentless effort to improve the offering and capture the largest market share possible. Now, I get that we don’t always want to do that. Sometimes we really don’t want to sell to SMBs because they have budget constraints and really aren’t mature enough. But what I’m trying to hammer home is that the culture of what we do with that information is what drives me nuts.

Extremely high performing organizations look at every loss as a stab wound. They triage it and figure out what moves they made that exposed them. They believe they are at war and feel that making a mistake jeopardizes their god-given mission. They weaponize the loss and turn it into energy to improve.

Bad performing organizations love the smell of their own shit and believe they’re building something akin to a cult where the customers are “lucky to have us”.

Don’t be like the bad performing organizations. Don’t be scared of worrying your employees by sharing what we need to change or improve on. Create best next action items from the loss on how to improve. Instead of building a culture of shelter from that loss, build a culture of weaponizing losses in to gains.

My Job is Me

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I had yet anther interesting and fun conversation with my colleague who sparked a fun question: why don’t people hire me because I’m Matt?

Here’s the back story. My colleagues and I interview a lot of different candidate each week. I think our average right now is probably 3-5 candidates a week ranging from entry level positions to director level. We’re hiring them for a specific job, such as Director of Engineering or Product Manager over a certain domain.

It’s always interesting being on the interviewer side because we get to briefly review a resume that has a list of accolades related to their history that maps to the job they are applying for. We often come in with strong assumptions around whether we are going to like the candidate or not. It’s hard not to be biased in these situations because we often know what we’re looking for and the words on their resume either map or don’t to the job description.

What we often find is that we’re wrong on our assumptions (rocket science level statement right there!). The problem is that we often really like the people we interview but they just aren’t a good fit for the existing role. Otherwise, we’d hire them in a heartbeat!

Part of what is tricky is that everyone has what they’ve done on their resume but there’s no context on how they got it done. That’s the art form that is missing. It’s not on there because it would look super weird and potentially off putting if someone said “Drove $5M in revenue through strategic political bachkchanneling” or “Rapidly pushed product through to the market by obfuscating a department through automation”.

Here’s the real ugly truth that’s a bitch to explain in reality: those traits are implied both in what an interviewee has delivered and how they explain that in the interview process. No one will every outright say that they had to make a massive political campaign to get the ball over the line, but rather explain it as “I influence the right people to move it forward”.

What we see is the job description and the resume. What we don’t see, and often don’t hear, is the art form in which they accomplished that.

For example, within product management, there are a ton of different ways to get the job done. There are general qualities that you want to look for but it really is an art form much like any other role. Product managers can be really strong on the quantitative analysis. They can be heavy on the business model side. They can also be a pure play product manager where they heavily focus simply on delivery to the market. They can be technically focused. The point is that they come in all different shapes, sizes, and expertise.

Now, I’m sure folks will argue that a product manager should have qualities that cover a wide range of the above skills sets. I don’t disagree but the reality is that individuals will skew in certain directions based on their education and experience. Finding someone who is well rounded in all of them is finding a unicorn and, I’d argue, someone that you actually don’t want because they are likely too shallow in each domain.

This goes back to the beginning of this post which is this: why can’t people hire me for me? It’s true that companies need specific skill sets at different stages of their life. But it would be interest to see a different type of hiring model where instead of hiring specific skills, we instead hire for art form styles of a domain. Meaning, we qualitatively look at an individual who has applied for a job in a certain domain (eg. UX, product, etc.) and identify how that individuals unique art form maps to areas of where the business needs.

There are some companies that do this by saying “we’re hiring product managers” and then map an individual to a product line of interest or art form need. Those are the minority, however, and it would be really interesting to see if both the employee and company are more happy than the traditional route of hiring.

At the end of the day, I want people to hire me – Ryan – because I have certain valuable skills but have an invaluable art form of applying those skills. I think that’s where the intersection of happiness between employees and companies may stem from.