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professionalism management conflict teamwork

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August 20, 2025 Score: 8 Rep: 3,710 Quality: Expert Completeness: 70%

You'll most probably need buy-in from your boss regarding this, otherwise your team will likely not want to join in.

I'd suggest proposing some form of "Hackathon" project with a set duration and expected outcome. Pitch this idea to your boss (include the aim, duration and how the company will benefit (in terms of cost-saving, efficiency gains and therefore revenue gain). To soften the blow somewhat, treat this as a "trial" and indicate that assessing the outcome of the project in terms of revenue gain is a part of the process. Remind your boss that efficiency gains = revenue gains.

You can then bring this to your team along with evidence of management buy-in.

Schedule this for a few days a month so that these hackathons don't monopolize BAU* activities.

You might well find that some of your team will be eager to learn new techniques and skills and others may want to just carry on doing whatever is within their comfort zone and forcing everyone to do these events might hit morale (and therefore responsiveness/performance).

A successful hackathon project will hopefully result in new things being learnt and injections of this knowledge into the team's collective processes and also (hopefully) expediate revenue gain.

  • BAU = "Business as Usual", aka normal working behavior.
August 20, 2025 Score: 5 Rep: 140,094 Quality: Medium Completeness: 30%

Make a business case.

It's your job to make sure software gets written to requirements within budget and schedule. You view the the world through the lens of software development.

Your bosses job is to make sure you all get a pay check. They view the world through a business lens.

The more you can speak your bosses language, the more likely they are to listen and understand.

You are asking your boss to make an investment, so you should quantify what that investment is (in money/hours/lost projects etc) and also quantity the return on investment. How much incremental future revenue will this produce over what amount of time and how much lost revenue does the business need to pay right now. Discuss the cost of attrition and hiring (if that's actually an issue).

Try a step by step approach.

You can start with a single "efficiency improvement" project, preferably one where the business metrics are relatively easy to track and that's relatively low risk. Most reasonable business leaders will be willing to tip the toes into the water and see what happens.

This builds trust and confidence: Once you have one or two (hopefully) successful smaller projects under our belt, you can start thinking taking on bigger stuff and discuss with your boss what level of oversight is appropriate.

If that works out well, you can target the final state, where you simply earmark 10% of the work time for "tools, education, concept development, research, etc."

Be honest during the analysis. It's possible that your boss is correct to be sceptic. I have certainly a fair number of "let's rearchitect to the current century" projects, which turned into a quagmire and where the promised "green grass" future never materialized. Like it or not, your old crusty code base has a lot of real life learning & hardening baked into it which is not easy to preserve.

I was planning on simply carrying out some of these changes in my spare time

This may be an option to break the ice, if your boss doesn't agree to run a small-ish pilot project.

Hi boss. As a proof of concept planning on doing XYZ and here is how I will track the result/outcome. I think this will save Y amount of $ or increase productivity by Z %. For this one, I can do this on the side on my own time, so it's not going to impact any ongoing work. If that goes well, we can discuss how to proceed in a more sustainable way.

"ask for forgiveness, not permission"

I would be careful to go behind your boss's back here. You want to build trust, but this can erode it.

August 20, 2025 Score: 2 Rep: 12,188 Quality: Low Completeness: 20%

Start with small and very small projects that are less trouble than they are worth. Simple "Proof of concept" projects that can fly under the radar yet have some internal use when finished.

Projects like monitoring, log aggregation, licensing, etc. Throw in an API and/or webhook.

This is how my team members got me to see the light when I was being hard-headed. As boss, it is easy to say no when you can visualize what is being discussed. It is hard to not green-light when you have a useful working example.