Let Me Tell You A Secret

In which I provide you with hundreds of dollars worth of software consulting, for free, in a single blog post.

consultingsoftwaremanagement Monday February 05, 2024

I do consulting1 on software architecture, network protocol development, python software infrastructure, streamlined cloud deployment, and open source strategy, among other nerdy things. I enjoy solving challenging, complex technical problems or contributing to the open source commons. On the best jobs, I get to do both.

Today I would like to share with you a secret of the software technology consulting trade.

I should note that this secret is not specific to me. I have several colleagues who have also done software consulting and have reflected versions of this experience back to me.2

We’ll get to the secret itself in a moment, but first, some background.


Companies do not go looking for consulting when things are going great. This is particularly true when looking for high-level consulting on things like system architecture or strategy. Almost by definition, there’s a problem that I have been brought in to solve. Ideally, that problem is a technical challenge.

In the software industry, your team probably already has some software professionals with a variety of technical skills, and thus they know what to do with technical challenges. Which means that, as often as not, the problem is to do with people rather than technology, even it appears otherwise.

When you hire a staff-level professional like myself to address your software team’s general problems, that consultant will need to gather some information. If I am that consultant and I start to suspect that the purported technology problem that you’ve got is in fact a people problem, here is what I am going to do.

I am going to go get a pen and a pad of paper, then schedule a 90-minute meeting with the most senior IC3 engineer that you have on your team. I will bring that pen and paper to the meeting. I will then ask one question:

What is fucked up about this place?

I will then write down their response in as much detail as I can manage. If I have begun to suspect that this meeting is necessary, 90 minutes is typically not enough time, and I will struggle to keep up. Even so, I will usually manage to capture the highlights.

One week later, I will schedule a meeting with executive leadership, and during that meeting, I will read back a very lightly edited4 version of the transcript of the previous meeting. This is then routinely praised as a keen strategic insight.


I should pause here to explicitly note that — obviously, I hope — this is not an oblique reference to any current or even recent client; if I’d had this meeting recently it would be pretty awkward to answer that “so, I read your blog…” email.5 But talking about clients in this way, no matter how obfuscated and vague the description, is always a bit professionally risky. So why risk it?

The thing is, I’m not a people manager. While I can do this kind of work, and I do not begrudge doing it if it is the thing that needs doing, I find it stressful and unfulfilling. I am a technology guy, not a people person. This is generally true of people who elect to go into technology consulting; we know where the management track is, and we didn’t pick it.

If you are going to hire me for my highly specialized technical expertise, I want you to get the maximum value out of it. I know my value; my rates are not low, and I do not want clients to come away with the sense that I only had a couple of “obvious” meetings.

So the intended audience for this piece is potential clients, leaders of teams (or organizations, or companies) who have a general technology problem and are wondering if they need a consultant with my skill-set to help them fix it. Before you decide that your issue is the need to implement a complex distributed system consensus algorithm, check if that is really what’s at issue. Talk to your ICs, and — taking care to make sure they understand that you want honest feedback and that they are safe to offer it — ask them what problems your organization has.

During this meeting it is important to only listen. Especially if you’re at a small company and you are regularly involved in the day-to-day operations, you might feel immediately defensive. Sit with that feeling, and process it later. Don’t unload your emotional state on an employee you have power over.6

“Only listening” doesn’t exclusively mean “don’t push back”. You also shouldn’t be committing to fixing anything. While the information you are gathering in these meetings is extremely valuable, and you should probably act on more of it than you will initially want to, your ICs won’t have the full picture. They really may not understand why certain priorities are set the way they are. You’ll need to take that as feedback for improving internal comms rather than “fixing” the perceived problem, and you certainly don’t want to make empty promises.

If you have these conversations directly, you can get something from it that no consultant can offer you: credibility. If you can actively listen, the conversation alone can improve morale. People like having their concerns heard. If, better still, you manage to make meaningful changes to address the concerns you’ve heard about, you can inspire true respect.

As a consultant, I’m going to be seen as some random guy wasting their time with a meeting. Even if you make the changes I recommend, it won’t resonate the same way as someone remembering that they personally told you what was wrong, and you took it seriously and fixed it.

Once you know what the problems are with your organization, and you’ve got solid technical understanding that you really do need that event-driven distributed systems consensus algorithm implemented using Twisted, I’m absolutely your guy. Feel free to get in touch.


  1. While I immensely value my patrons and am eternally grateful for their support, at — as of this writing — less than $100 per month it doesn’t exactly pay the SF bay area cost-of-living bill. 

  2. When I reached out for feedback on a draft of this essay, every other consultant I showed it to said that something similar had happened to them within the last month, all with different clients in different sectors of the industry. I really cannot stress how common it is. 

  3. “individual contributor”, if this bit of jargon isn’t universal in your corner of the world; i.e.: “not a manager”. 

  4. Mostly, I need to remove a bunch of profanity, but sometimes I will also need to have another interview, usually with a more junior person on the team to confirm that I’m not relaying only a single person’s perspective. It is pretty rare that the top-of-mind problems are specific to one individual, though. 

  5. To the extent that this is about anything saliently recent, I am perhaps grumbling about how tech CEOs aren’t taking morale problems generated by the constant drumbeat of layoffs seriously enough

  6. I am not always in the role of a consultant. At various points in my career, I have also been a leader needing to sit in this particular chair, and believe me, I know it sucks. This would not be a common problem if there weren’t a common reason that leaders tend to avoid this kind of meeting.