How to Get Your Leadership to Say Yes to Investing in Your Professional Development

It is not easy for most of us to ask for help or money. Often, the leading blocker holding leaders back is some sort of fear. Unknown fears can keep us from even taking a step into the uncomfortable to objectively seek to understand the problem our team is facing, which means our teams will continue to operate at sub-optimal levels.

Face your Fears First

It is good to first take a step back and become self-aware of what might be holding us back from understanding some concerning trends on the team. It’s hard to think clearly about a problem if blinded by subconscious fear. Get curious about what is coming up for you by asking yourself some of the following questions:

Are you trying to be perfect?
Is there someone you are trying to please?
What is a time in the past that you had a similar situation and you successfully navigated through it? What did you do then that might help you now?
Imagine the worst-case scenario, and what ideas could help you avoid that from happening?
Or, visualize a happy outcome, and talk through with someone what steps led you there.

In doing this, you are becoming comfortable with the uncomfortable. You can start to outline some next steps to understand how to face your fears and ask the right questions that lead to discovery, solution identification and action.

Problem and Solution Identified, Now What?

Leaders often get stuck here. In our previous blog, we discussed how to build a business case. During this process, it is important to identify who has the authority to approve the budget for the business case, and who the project will impact. When mapping this out, you will often find leaders who are both impacted and need to approve. Once you have identified who these are, reach out to them and include them into the process of building your business case. Before your discussion meetings, be sure to plan in advance, so you can tailor your conversation to the audience.

Get to Know your Audience

For each key individual you plan to speak with, create an outline of who they are in preparation of your meeting. You can do this by answering the following questions:

Is this individual an early adopter and open to change, or typically avoids change?
What is the key business objective this person is currently focused on?
What motivates this person? What do they value? What do they care about?
How does your proposed solution positively help this individual more effectively, or efficiently obtain their key business objective?
If we don’t focus on this solution, what will block us from successfully meeting business critical quarterly targets?
How does this person best communicate and take in information? Do they need to see data in advance, and have time to reflect before the conversation? Or, do they like to brainstorm and want to feel like a key collaborator?
What is the authority approval this person has in the final purchase decision?
What questions or objections do you anticipate they will have about your proposed solution? How do you plan to respond to these?

In answering these questions in advance, you now may see common themes that build into your open questions and speaking points for the agenda of the meeting. You may see some commonalities amongst the key individuals and decide a group meeting might be better. However, if someone is typically negative to change and is the main budget approver. You may want to have a pre-meeting with them, in which you just ask open questions to obtain better answers to the above questions. You may want to ask questions that guide them to self awareness around the problem, and get their insight and feedback into the solutioning in order to obtain buy in.

Understand the Budget Appetite

As you step through these conversations, you want to be respectful, and transparent. You don’t want individuals to feel like you are going around them. The goal is to create a shared common objective and collaboratively build a business case that already has your approvers buy in.

As you move to build the business case, you should naturally get a sense for the budget appetite of the individuals. In your conversations with them, you should have a sense for the following:

Is there a budget range we can work within for this?
What have we typically spent in the past for similar sized projects?
Is there budget left unused that we could reallocate for this project?
Is there anyone else who needs to approve, that maybe you missed?

Be sure to ease into the budget conversations, at this point they should have a sense of the shared common pain and gap, and that without this solution no one will be successful in meeting their targets.

Crossing the Finish Line

If you have made it to this point, you have been working with your key approvers to obtain feedback and buy in into the creation of your business case. You know the budget range, and the approval chain. If you sense hesitancy, remain curious and ask open ended questions to understand what remaining questions may be keeping you from a Yes. It may be as simple as the group is risk adverse, and wants to try out the solution with a pilot group first. Adjust your business case, accordingly, and then work to finalize. This iterative approach will help your case be stronger, ensure you didn’t miss any blindspots, show your ability to influence cross-functionally and bring people together to create a win/win outcome.

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