How to make your boss care about your initiative

For all the effort we put into our work, even work that has been prescribed to us by our boss, it often seems like, regardless of progress or success, our stakeholders are often distracted by other priorities. It’s frustrating. After all, they told us to do this work. It must be important and yet they’re now distracted by the latest priority, market shift or revenue numbers. Keeping our work relevant and visible to our stakeholders is critical to ensure we’re always doing the work the company should be focusing on right now. In addition, it ensures we’re aligned with the rest of the organization and the teams around us. How then do we make sure we maintain our boss’ attention as we work towards our goals? Here are two tips you can use: connect your work to their goals and be proactively transparent. Let’s take a look at both. 

Connecting your work to your boss’ goals

Even if your work was assigned to you as a list of requirements to deliver by a deadline, one of the most powerful things you can do at the outset is to reframe that work as a business problem to solve. Sharing that problem statement back with your boss ensures that you’re not just building things but also helping them be more successful. You can take this a step further. In your problem statement ensure that you are stating clearly how the business problem you’re solving is manifesting and how that customer behavior is negatively impacting the business. 

Let’s say that your getting users to sign up for your service, they use it one time and then they don’t return. Your boss told you to add a sticky feature they saw on a competing service. You then reframe that requirement back to your boss acknowledging that currently your service is causing users to try the service once and then not return. In addition, you’re going to point out that this is causing an increase in your acquisition costs, onboarding costs and reducing your profit margin.

This is a great start. You’ve now connected the work your boss asked you to do with their success criteria. Now, take it a step further by getting more specific with data. How frequently does the problem happen? How many users does it impact? What are the per-user acquisition costs and how do those multiply as we have to back out to the market to acquire new ones? Finally, what’s the impact this business problem has on profit, exactly. By setting these baselines with your boss your illustrating that you have a clear grasp of the problem and the impact it’s having on the business and their personal success. The specificity with numbers is the key to grabbing their attention. 

Be proactively and radically transparent

Now that we’ve set the baseline with your boss and they’re aware that you understand why they asked you to build the competitive feature you need to start keeping them aware of your progress. As you can imagine they have a thousand other distractions, yet you laid a foundation of conversation based on their success. Continue that thread with regular, proactive, transparent communications about how your work is progressing and most importantly how your team is trending towards the performance metrics you outlined in your business problem statement. 

Whatever your boss’ preferred communication method is, use that to let them know, at least on a weekly basis, how you’re progressing. Keep it short. Focus on three points:

  1. How are you progressing from baseline towards the target metrics
  2. What you’ve shipped since the last communication and the most important thing you’ve learned so far
  3. What you plan on doing next and why

That’s plenty of information for a time-poor executive. They didn’t ask for this communication but it keeps them aware of the work, its progress and contribution to their personal success. As new or important information arises, flag it in these communications and if it requires executive intervention, let them know you’ll be reaching out for a meeting. 

Make them a hero and they’ll pay attention

Essentially, you’re making your boss a hero. In all likelihood they’ll pay more attention to your initiative if that’s how they feel about the work you’re doing. Your job is to ensure that as you make progress, adjust course or make unexpected decisions you’re always communicating it and keeping it clearly tied to the original goals you’ve set in your problem statement. Give this short recipe a try and let me know how it goes. I expect you’ll start to see changes very quickly. 

Books

Jeff Gothelf’s books provide transformative insights, guiding readers to navigate the dynamic realms of user experience, agile methodologies, and personal career strategies.

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