How to Find a Good Boss

Nigel B. Peck
Sep 23, 2019 · 8 min read

I wish I knew. Where do I begin?

Photo by bruce mars on Unsplash

Sunday, September 15 2019

I recently took a position as technical project manager with an unnamed startup. Not much need to protect anonymity here, since after a week I still have no idea what company I’ve been working for.

It’s basically freelance, although full-time and then some, paid week to week, and very early stages. I was brought on board as Technical PM by the CTO (for want of a better title since he doesn’t have one) after working on a data manipulation project for him and impressing him with my approach.

I was told that clear communication and organisation were expected for someone in my position. I agreed wholeheartedly, assuming without question that that went both ways (as it turned out, very much wrongly).

He was desperately in need of support in finding new developers and managing existing ones. I started last Sunday, understanding there was no time to lose and everything was behind. I did seven hours on Sunday and by invoice time Saturday night had logged sixty four.

In that time I found new lead developers for the two core technologies used (Laravel and React Native), on-boarded them, developed working relationships with a diverse remote team, evaluated and renegotiated arrangements with existing developers who had been short on oversight (as had everyone), had two prototype apps developed from existing mockups, planned and implemented a migration of the core APIs to a clean and appropriate architecture, which was desperately needed, began forming plans for release management and QA, and generally formed plans and management processes to support the creation of quality software going forward.

In this time I had one actual conversation with the CTO. On Sunday when I started I was told he “didn’t have time for any big six hour handover”. I made it clear that regular catchups were necessary to cover queries I would inevitably have, and that clear communication would of course be forthcoming, which from me, it always was.

The rest of our communication was all through Slack. It took until Thursday to get an answer on what the product was that we were actually building (not for lack of trying), by which time two prototype apps were expected to be completed (actually those were initially expected for Wednesday, including sourcing new developers for each). Spec was virtually non-existent, and questions regarding what was needed were met with an attitude of why don’t you know this (note to self: must improve psychic abilities), when they were answered at all. When I finally drilled him on giving me some concrete info about the setup, and gave a clear picture of how little I knew, his response was that it was so easy to not realise how much other people don’t know unless you tell them. Duh. Skipping “six hour hand-overs” does not come without implications.

Developers were given hastily written lists of half-developed ideas, dropped in to Slack channels, and then expected to be berated when they weren’t finished by yesterday. This, of course, was not something I did. Many of them had been on board a week or two.

I was told that all communication with developers was direct, since bringing them together in the past had caused problems. There had been a lot of “churn” which worried those who stayed around.

Repeated requests for quick calls to get me up to speed were ignored or put off to the eternal “tomorrow”. By Friday it was meltdown, since apparently a demo API was needed for Saturday, not that I had been told about that previously, which I still had only a 30% appreciation of what it should do. It was essentially suggested it was my fault it was not ready, although quickly withdrawn at my stunned response. Presumably a convoluted message earlier in the day to say, get on to so and so and make sure this is ready today, it’s priority over the migration, that I had no idea what it was that was supposed to be done, or how to know if it was, is what that was referring to.

Once meltdown came on Friday night, I regardless did everything I could to make it right, albeit with no clear idea what it was that was needed, and the complete disappearance of said CTO following messages to say it had happened. After spending three hours fishing in the dark and emailing said so and so to get his attention, during the small hours of the morning for him (which he actually responded to and did what was needed), trying to set up a server using a setup process which was always described as “working just follow it” but nobody save the CTO found that experience, it was finally resolved when said CTO reappeared and gave some answers to queries, oh just do that if that happens (again with the lack of psychic abilities). Well yes, but that’s not in the document is it.

How can a supposedly highly experienced CTO not get this? All of this and everything else would have taken a fraction of the time, and been done much more effectively, had time been taken to participate in short calls, as requested, explaining what was needed and how things were set up.

I had seen some payment issues coming up with a number of developers during the week, payments were two weeks behind in some cases, many waiting on assessment due to numerous concerns about poor work, with the developers expected to keep producing and not being aware of any concern.

This led me on Saturday to raise concern about payment issues, which was met with incredulity. I expressed concern over my own payment, since I was completely at risk with no prior experience to trust, and over sixty hours by this point, which was met with an appropriate response from him (it certainly wasn’t all bad, he could be very professional and encouraging in many cases). I said an immediate payment was not necessary, I would invoice that evening as arranged, and left it at that.

I invoiced on Saturday night, and fully expected to see the close to five figure payment on my email the following morning, his timezone being seven hours ahead of mine, and a full day of work ahead on Sunday. Surely he wouldn’t expect me to start another full day at 6:30am on Sunday without the peace of mind of having being paid for the first seven days, especially after our conversation on Saturday and his offer to make a payment immediately at that point (“I can do two grand, that’s the most I can do without my card reader”).

So I wake up on Sunday morning. Nothing. No response confirming receipt of my timesheet, no mention of when payment is being made, just a note that another developer has been paid (one of those who had been waiting two weeks, and had now refused to deliver an APK that was needed desperately until payment was forthcoming). He was supposed to have been paid the day before, so APK could be delivered as urgently requested for Saturday, for a demo I still have no idea if it actually happened or who it was for, despite committing all of my Friday night to resolving issues that could have been resolved in five minutes with two minutes of proving information. Perhaps I mentioned that. Sorry to rant, but… you know.

Which brings us to Sunday. Enough was enough. The complete lack of clear communication or support could not continue. The failure to deliver peace of mind to a new tech PM who had dropped everything to get the job done, despite having just moved house, was simply a symptom of that. I messaged said CTO and expressed my discontent, explaining that there would be no more work forthcoming (“not risking another minute”) until I had been paid and had discussed progress and plans over a voice call, particularly needing to discuss massively improved communication if this was going to work going forward. This took hours to be responded to as usual, and was mostly ignored (also as usual) by which time I had disabled Slack notifications and messaged to say that email or phone would be necessary for that reason.

When a WhatsApp response finally came, I was to understand that there were some messages on Slack to peruse, but what “made him most angry” was the disabling of Slack notifications. Apparently if a team member had done that I would have sacked them. At 10:30am Sunday morning, local time, following sixty four hours of work that week, I made it clear this was mistaken, that there was no actual requirement for me to be on call, although of course I would have been under normal circumstances, which he had ample proof of by this point, following many days of instant responses on my side from 6:30am to midnight. To him or to any team member.

It was made clear that payment was coming, but I needed to get back on Slack. I made it clear that there was no possibility of that happening until I had had a voice conversation with him, and, of course, been paid. Payment arrived a few minutes later, around 11:10am local time, with no message or response on WhatsApp confirming it. And certainly no call to chat.

Three hours later, a response complaining about my lack of confirming receipt of the unannounced payment, and taking issue with my unhappiness about not having it first thing, arrived on WhatsApp. The irony of totally ignoring my concerns about poor communication from his side seemed to be completely lost on him.

Apparently he could “speak within the next few hours”. This was 1:51pm, local time for me. Clearly the unspoken implication was that it was now time to be back on Slack, having been paid. As we both knew, there was a lot of urgent stuff to take care of, with partially completed migration and pending QA of app deliveries. I responded within a minute as usual, laying out my concerns in more detail regarding communication and what was needed to make this work going forward, and for me to continue.

Certainly with candor, but looking towards the positive and how it can be resolved going forward.

As I write this the time is 9:00pm, no further messages or calls have been forthcoming. I have had a most welcome, relaxing Sunday, and still have no idea what messages await my perusal on Slack. Why a CTO, who now has his plate cleared of around a dozen developers and numerous project management and administration commitments, is unable to spend time on a short call with his technical PM each day, also remains a mystery.

Perhaps it always will.

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