What types of management problems plague startups?

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Being an avid reader of Fred Wilson’s AVC, I’ve learned much over the years. And one thing he underscores is that *ideas* are a dime a dozen. And that great investments are in team & execution.

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As a long time consultant, I’ve had the good fortune to see a lot of startups under the microscope. If you work a FT role for 2 years, over a decade you may work at 5 companies. In the same amount of time, i’ve worked at over 65 companies.

In those years I’ve encountered great teams that are super organized, and continue to move the product forward. But I have also seen a number of symptoms, that caused the business problems, and slowed down their march forward.

Low morale

One firm I worked at a few years back was in the space around education, specifically with a lot of microlearning products, with big customers doing corporate onboarding.

Their sales team was world class, closing bigger and bigger deals, but engineering had terrible and festering problems. As it went, they grew to have hundreds of employees in a matter of a year or two. Meanwhile the CTO was not a big people person. He didn’t like speaking in front of large groups, nor was he very hands on. As a small ten person startup he was super technical and talented, but as the company grew so fast, it left a leadership vacuum.

And then some bad hires grew the engineer team fast. But internally there was a lot of infighting. The original founding team worked hard and had strong direction, but the new hires all vied for control. And the ugly personalities reared their heads.

After a few short weeks, half the engineering team quit, in a matter of days. A tough blow to a team already struggling to keep up with growth.

It is not easy to right a large plane in mid flight like that, carrying plenty of technical debt besides.

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Bad alignment

Another place I had the pleasure of working at was a well known digital media brand, that expanded into film production, recording and even investigative reporting. For all it’s wide ranging efforts, it presided over a huge growth business, with seemingly unlimited revenue. Impressive to be sure.

On the technology side, however things were not so sunny. As their business grew, they planned to consoldate data from many disparate divisions. And this is a process that many growing businesses go through. Finance in one platform & database, bookings & production in another, while analytics and viewer statistics in yet a third. But how to report on all of that data?

As a special crack team of big data experts, we were assigned the task of building out this centralized repository of business truth. And as we built and architect that system, we needed to work closely with the operations division.

Now in this business, they were using public cloud, Amazon Web Services like many other startups. However they had a separate team of devops who presided over these accounts.

As our team was handed strict deadlines to deliver working reports & systems, we had conference calls with the Devops team. However that team was not on board with those deadlines. They pushed back and claimed such systems would take months to setup.

As we explained expectations being pushed on our shoulders, Devops said “just push back and say no”. They advised that we “send it back up the chain”

But what if there’s a chink in the chain?

Clearly the two teams were not aligned at all on deadlines & deliverables. And that’s not a fault of either of those teams. It straightaway falls in the lap of management to align those.

And we were somehow stuck in the middle. Ugh!

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Loose discipline

One startup I worked at had a security and authentication app.

Here teams were fairly happy on the whole. In fact they raved about having a great boss. Indeed the boss was a very kind leader, understanding, patient, and hardworking.

However, over and over, we lacked a “decider”. Here other team members were giving each other tasks. Promises were made loosely, and then forgotten one or two weeks later. And a constant lack of direction dragged down delivery.

For my money, a promise to have a meeting at 10am, is one all parties should abide. Whatever their level in the business. Not be late, have excuses about trains, or simply skip the meeting with no explanation. These types of habits cause the team to grow weary, and lower the bar of expectations.

Frustrating indeed.

Related: When you have to take the fall

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