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How a software selection taught lessons about the next generation of leaders

Den Howlett Profile picture for user gonzodaddy June 19, 2018
The next generation of leaders is different from mine in important ways. This is proving valuable as we get ready for our next iteration.

The last month or two, I've been deep into a multi-tool software selection process. It's for ourselves. Along the way, I've learned many lessons. The most important one is about what matters to the next generation of business leaders. These folk are fast coming up the track and ignoring them is foolish.

Five years into the business and it's time to up our game. We are pretty good at ad hoc social amplification and our email newsletter capability is OK. But as we think about multiple and growing channels of communication and distribution, it made sense to rethink the what, where, how and why of the tools we already use.

An inventory of those tools proved illuminating. One tool, in particular, we use for content distribution has grown to be loathed. How do I know? It barely gets used. Another tool has proven troublesome in light of GDPR and so is another favorite for review.

We haz Frankensoft

Like many other businesses both large and small, we have acquired services that leave us looking a bit like the house the Topsy built. Frankensoft is how Brian Sommer would describe it.

Inventory completed, we immediately saw the potential for released resources. But if you're going to invest, the last thing you should be doing is looking at like-for-like systems. That's a road to nowhere but a surprisingly common mistake we bucket under 'lift and shift.' Similarly, it is getting increasingly difficult to know what tools will be required two, let alone five years down the track in what is a fast-changing environment.

When I consider the evolution of our own tech estate, it has gone from a small handful of free or very cheap offerings to, in some cases, full-on enterprise-class software, at nosebleed enterprise-class prices. Those have been conscious and, as it turns out, very good decisions.

As we've gone through this process, I've had to think through the way in which our processes change (and how that translates into benefit the team can buy into), personnel requirements, business value metrics and so on. The team has thrown ideas and requests into the pot too. As with all these kinds of project, it is multi-faceted with levers that don't all pull in the same direction at the same time.

For the big chunk of work, I developed a short list of four solutions that might meet the grade. But it was when I submitted my initial findings report and testing results that the 'next generation' issue cropped up.

I was already aware that there needs to be a balance between functionality and a pleasing UI. But as every buyer knows, those tradeoffs are not easy. As an enterprisey type, I tend to favor function over good looks. Even then, I knew compromises were required but hoped I could 'sell' what looked fit for purpose back to the team.

The next generation speaks

One of our guys who is normally a quiet individual suddenly buttoned me and asked if I had considered other tools. No, I hadn't, largely because they had not come up on my radar. But I was willing to give them a shot as it was clear he had a good case for evaluation, contextualized around modern working practices. I was still conflicted over a final decision - fearing the dreaded 'no decision' and more time trying to solve the problem so in that sense, it wasn't a hard decision to at least take a look.

I immediately understood what he was after, a great UI with enough functionality to get the job done. Equally, he was happy to defer to my understanding of functional requirements if that meant rejecting his finds.

His number one pick was really, really good looking with a great deal of potential. It was eye poppingly good at a good price point. But, there was a deal breaker piece of functionality the vendor agrees is needed in our use case but is missing. We tried a workaround but it left us looking at a confusing solution that for all its good looks would likely fail very quickly.

This process also raised an interesting question. Who could we find that would make this thing fly? We all realize it needs to be a creative person and as we further discussed the problem, it suddenly struck all of us that we must actively find someone who is of that next generation of leaders.

From everything I can see, the next generation of leaders is much more creative than mine. In my words - they have better ideas than us old farts. They are also mighty fine storytellers, something that is very close to our hearts. This recognition is exceptionally good news.

It means we can bring an entirely fresh set of eyes to what we're about, learning about what matters to them, how they want to consume content, what types of content they want to consume and so on. This will help us and our partners immeasurably. I certainly expect to experience some intellectual pain along the way, but that's OK as long as we're learning.

Where are we now?

We 'think' we've got a solution in sight with which we can all live. At least for the time being. We know this decision might not be one for the long-term. That's OK since we understand the compromises involved.

The upside is that the chances of getting adoption across all the processes involved are now much higher than was the case in the middle of this journey. In short, the business case looks better than was originally thought and is a lot clearer in scope and anticipated outcomes. We're also keeping an eye on what happens with the solution we dropped. If what we're told about roadmaps turns out as promised then who knows, we might switch.

That's not a bad result from what started out as a software selection problem with lots of fuzzy questions surrounding it. It's an outcome that leaves the whole team feeling very good about what happens next.

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