Tech Team Check-Up

At Upspark our goal is to help Toronto startups do better. We help their technology teams grow and scale, avoiding the many common pitfalls that lie in their path.

Many of those pitfalls are born in the communication between the senior leadership and the development team. Translating mission statements and business objectives into development tasks requires patience and judgement, and it can be hard to keep that connection clear as tasks pile up and fires break out.

To that end, we’ve come up with a set of powerful questions that can help reveal when those connections between the strategy and the tactics have broken down. If you’re running an Engineering team and you feel like there’s some friction between you and the senior leadership at the company, try sharing these questions with your executive to spark a powerful conversation.


The Questions
1. Does everyone in the company understand the company’s mission and key business objectives?

We do this as a straight-up Yes/No question. Forcing people to take a stand on one side or the other almost always reveals that the real answer is “No,” or even more alarming, “We aren’t sure.”

We’ve talked before on this blog about ways to compose a powerful mission statement. Even if you’ve written a mission masterpiece, though, it does no good if it’s not understood and internalized by the team. Likewise your business objectives: just having them isn’t enough – they’ve got to be a part of how the team makes decisions.
When the answer comes back “We aren’t sure,” that’s a sign that nobody’s checked with the team to assess their understanding of the mission and objectives. You’ve got to know that they know.


2. Who is responsible for each objective and what is their ability to deliver against it?

List out each business objective your company is pursuing. Who is responsible for that objective? At the end of the day, who makes the final decisions regarding budget and resource allocation against that objective?

And what is that person’s ability to deliver? Do the necessary teams report to them? Do they have sufficient budget? Can they hire if they decide that’s required?
These things all come down to money and time. If you don’t control those, your ability to deliver is compromised.


3. Which key business objectives is the Engineering team meant to drive?
How often do those objectives change?
How is the team’s success measured?

Not everything that gets done at the company is on the Engineering team, presumably. Making sure you and your boss have the same impression as to which subset of those business objectives is your team’s responsibility is crucial.

A high rate of change in objectives is a good sign that something is going off the rails. Even in a startup, where of course objectives have to change with regularity, constant changes in direction will leave the team bewildered and disheartened.

Measurement of success is a common pain point for engineering teams. Simply delivering bug fixes and features turns quickly into a meaningless grind, divorced from those business objectives that we thought were so important.


4. How are business objectives turned into Engineering tasks?
Who determines the priority of tasks?
How is the required investment agreed on and measured against?

Now we go down one level. This question moves us out of the usual sphere of knowledge for your executive, but asking them for their impression of how this works can reveal fatal misunderstandings. If your CEO thinks it’s their job to prioritize tasks, well, that’s a really good thing to know, I guess.

Agreeing on the required investment had better involve the people whose time is going to be invested, who are closest to the problem and understand the space in which the solution will be built. At the same time, what happens when estimates are not met? How are team members held accountable?


5. What factors most limit the capacity of Engineering to work directly on those business objectives (choose the most limiting):
  • Context switching
  • Deployment/testing
  • Fixing production bugs
  • Unplanned or emergency work
  • Technical debt

Note that nowhere do we provide “not enough engineers” as a factor – this is about what is costing the current team’s productivity. Here is where a CEO in most companies will likely have very little idea what’s going on, but if you can get them here, there’s a chance to open their eyes to the tradeoffs necessary.


The Conversation

It’s our experience that these questions, seriously considered, will often spark a powerful conversation between senior leadership and the technology team. When engaged with honestly and thoughtfully, they can lead to surprising insights as to where gaps are appearing in your organization.

Have better conversations, create easier decision-making, and let your teams accelerate their productivity. Download a printable form you can take into a meeting!

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