• Peter Gross

Q&A: My Answers to Common Questions Nonprofit Professionals Ask Me

During my years in the nonprofit industry, I’ve worked with nonprofit professionals at various career stages and levels in their organizations. Every role has its challenges, and throughout my years as a consultant and now as a coach, I’ve helped clients navigate several that seem to emerge time and time again.

In this post, I’m sharing the answers and advice I give in response to three career questions nonprofit professionals often ask me.

“How Can I Get My Boss to Make a Decision?”

There are many scenarios in which your supervisor’s lack of a decision or direction might hinder your ability to move forward. As frustrating as the situation may be, there are practical and constructive ways to approach the issue.

Have Compassion

Try to move past any frustration or irritation you might be experiencing and focus on cultivating compassion for your boss. People rarely avoid making decisions just on principle or spite. It is more likely that your superior is encountering some sort of difficulty in navigating their decision and establishing an answer they feel is sound or that they are confident in.

There are various reasons your boss might be struggling to make a choice. Here are a few common ones:

  • They cannot accept the idea that their decision might not be the “right” one.

  • Decision paralysis, or being consumed with worry over how others will view their decision.

  • They are having difficulty giving up the alternative to their choice.

Offer Choices

If there is a delay in your boss’ decision that prevents you from making valuable progress in your role, you can aid them by providing them explicit and informed options. Simplifying and fortifying how you present the choices will help them assess and make educated decisions.

  • Be Succinct: When sharing options for your boss to consider for their decision, be brief, clear, and concise.

  • Be Specific: Make sure to identify exactly what each choice entails and its anticipated outcomes.

  • Present Pros and Cons: For each choice you share with your boss, present the expected benefits as well as realistic drawbacks. Even if you are making a recommendation, presenting the pros and cons for each is both more honest and will build trust that you have looked at both sides.

  • Risks of Inaction: As part of your presentation of choices for their decision, share what you expect the consequences of not acting on a decision to be.

Get The Whole Picture

If you are frustrated by your boss’s indecision, consider speaking with them to understand their fears or concerns. If you are not comfortable talking with them directly, you might also talk to colleagues and peers familiar with the situation. Learning about the obstacles keeping them from making a decision may reduce the stress you’re experiencing. It might also help you develop a plan as to how you can work with them to make progress.

Do Not Force It

As challenging as it may be, especially if your boss’ lack of decision is creating challenges for you, you have to remember that you cannot force their decision. Do your best to provide valuable insights and solid choices and make yourself available to support your boss through their choice as needed.

Let It Go

Once you have done everything you can to inform your boss, it is time to let go. Focus on the aspects of the situation you can impact and then let the decision go. I know that it can be challenging to admit you are powerless over your boss and that, ultimately, you do not have control over the outcome of this scenario. You are only in control of your contributions. Rest assured that you did your job and move forward.

“How Do I Ask For Productive Feedback?”

Feedback can play an essential role in nonprofit professionals’ career development. The challenge is asking for that feedback and ensuring that it is clear and constructive. Though it can be intimidating and potentially nerve-wracking to ask superiors for feedback on your work, productive feedback is incredibly valuable to your growth in your current and future roles.

How Asking For Feedback Benefits You

If you are hesitant or uncomfortable asking for feedback, keep in mind that it is advantageous to get the information you need to excel. Requesting feedback on a regular basis (and acting on it) will allow you to receive input that you can use to improve your performance, but you will also experience the reward and satisfaction of advocating for yourself and your growth.

How It Benefits Whom You’re Asking

Asking for feedback is not just a positive step to take for your career growth. It is also beneficial to the person you’re asking.

The person you are asking for input on your work will experience a positive reward. Whether or not you articulate it, you are communicating to them that their experience and perspective are valuable to you. Asking for their assessment of your performance shows them that it matters to you and is significant in your experience working with them.

Asking for specific feedback can also alleviate any anxiety or discomfort your boss has about determining what feedback to give you. By posing the question and requesting input on a particular aspect of your work, you are providing them a structured and targeted space to discuss their thoughts.

How Nonprofit Professionals Can Ask for Feedback

Ask Explicitly

Asking for specific input on a particular task, project, or aspect of your work will prompt the most helpful feedback from your boss. For example, instead of saying, “How am I doing in my job?” a question such as “Can you provide me feedback on how I facilitated that meeting?” will provide more productive insights.

Ask Broadly

Seeking multiple points of view from individuals you report to and collaborate with will give you a well-rounded picture of how your work is perceived. It will also help you avoid feedback influenced by unconscious biases. Plus, getting multiple opinions on your performance will allow you to synthesize and develop your own insights and ideas on making improvements. The research on the brain tells us that both being open to feedback and using that feedback to facilitate your own insights is an extremely effective way to change and grow.

Ask Often

Do not save your requests for feedback for your annual review or quarterly performance assessments. Instead, ask for feedback as soon as possible after the task/project/event has concluded. And, by building a habit of regularly asking for feedback, you can make minor course corrections that create more impactful improvements to your work.

Regularly asking for feedback, and doing so in a timely fashion also reduces stress for the person from whom you are requesting input. It reduces the weight of the request and simply makes it easier for that person to provide accurate input.

Think of it this way: If I balance my checking account once annually, the anxiety of learning how much I have spent is more significant, and I miss the opportunity to make small corrections throughout the year. However, if I balance it monthly, I can identify fraudulent transactions earlier, change my spending habits efficiently, and keep my money anxiety at a lower level.

“What Can I Do to Get the Nonprofit Professionals Who Report to Me To Manage Their Constituent Relationships More Effectively?”

I have seen nonprofit leaders struggle with helping their teams develop essential routines and habits on many occasions. The challenge of working with direct reports to capture and log their constituent interactions (donors, volunteers, program participants, etc.) quickly and accurately is a common one! The conclusion of, “They should do it because I told them to,” is an understandable one. However, there is more to establishing a habit such as this.

When you want someone to do something different from what they are currently doing, you essentially ask them to cease an old habit and replace it with a new one they will establish. We all know that bad habits can be tough to break, and new ones can be difficult to learn and stick with.

In this scenario, referencing the habit formation loop will help you understand how to guide your direct reports to the new habit you request of them.

The Habit Formation Loop

  1. Trigger: Help your team identify the trigger or the cue that will prompt their brains to start an action.

  2. Action: Be explicitly clear about what action your team needs to carry out and how they should do so. This might be a cognitive, emotional, or physical action they perform.

  3. Reward: A reward reinforces a set of actions or reactions and is valuable and memorable. Be creative with what rewards apply to your team.

How to Apply The Habit Formation Loop to Managing Constituent Information


When it comes to helping your team establish the habit of capturing information about their important relationship building, the trigger might be the interaction with that constituent - a phone or video call, email, letter, or in-person meeting (if you remember what those are) or even the scheduling of that call or meeting.


If the trigger is that interaction itself, the action requested of your staff could be immediately recording the results of the interaction with the donor in your CRM or another system.

If the trigger is the scheduling of the interaction, the above action could be made even easier if you encourage them to build a 15-minute buffer in their calendar after every meeting to make space and be prompted to take the action. Similarly, you might encourage them to block off 30 minutes on their calendar to record information from that day’s interaction.


There are several ways to reward your staff. You might consider:

  1. Reviewing entries daily or weekly and sending a thank you for consistent entry.

  2. Reviewing entries daily or weekly and offering helpful strategies or tips to help move that relationship along.

  3. Holding an informal contest where direct reports who enter a certain number of interactions or are consistently up to date is eligible for a small gift.

Continuous Learning and Adjusting

None of these strategies are guaranteed to work the first time. After you have implemented a change, make sure to monitor the results, seek frequent feedback on how it is working and make adjustments as needed.

While nonprofit professionals and leaders face occasional challenges in their roles, there are always solutions to be found through careful assessment and productive strategy. I hope my answers to these common nonprofit industry questions are valuable to you.

Do you have obstacles you frequently encounter in your nonprofit work life or career? Please feel free to contact me with your questions.

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