Generosity is not just sharing value, but making that value obtainable

It’s a bit of a cliche, but I found being generous is one of the most important things that I can do. However, there is a lot of confusion on what is generosity. What I found is generosity is not just offering value from yourself. I offered too much of myself in the past, and it hurt me. Generosity is offering value to another with boundaries that both ensure that I can provide the value and limits the investment from the other to receive the value. It’s not offering the impossible promise, “I will do anything for you.” It’s helping any way you can at the time.

The value of generosity is tremendous. When someone is generous to me, I feel a wave a gratitude. I was given exactly what I needed for nothing! When this wave of gratitude hits in the context of trying to achieve an audacious goal, it’s an affirmation that boosts inspiration. This compounds and the goal becomes a reality. As my goal becomes a reality, all I want to do is share the benefits of achieving that goal with everyone who helped me along the way.

This is the high-level view of the virtuous cycle discussed in so many startup communities. Whether it’s the lore in Silicon Valley or #givefirst in communities touched by Techstars, this virtuous cycle, catalyzed by generosity, is critical to success in these communities. The problem is that it could take years to experience this virtuous cycle at a high-level.

So I am going to breakdown how generosity can happen several times in organizing a single meeting. It is important to remember that the definition for generosity in this essay is delivering value for such little investment from the other party, that there is a high ROI for engaging with one another. Generosity also spurs emotions of gratitude and inspiration. The hope is to recognize generosity in the seemingly benign things we do everyday.

An introduction: Ask a specific, interesting question

There is one sure fire way that I found to get in touch with anyone, whether it is an expert or an investor, it is to ask a specific and interesting question. It does not matter if I know the person already. If I know someone already, they might meet with me without a specific, interesting question, but I rather not waste their time.

Asking an interesting and specific question is the first act of generosity in a meeting because it is offering up something we all crave, something interesting, for a very limited investment. This is a value proposition hard to deny. We spend most of our waking hours looking for or doing things that interest us because that’s what satisfies everything beyond our basic needs. Being specific is important because it limits the investment necessary to get the value of answering an interesting question. The ROI is so high, it’s almost irresistible not to reply.

It takes a tremendous amount of generosity to offer an interesting and specific question. There needs to be an understanding of what is interesting to the recipient. This is done through research, whether it’s reading blogs or acquiring knowledge over time. Then, establishing the boundaries with specificity takes an understanding of what is truly important. It should isolate the critical information that enables the next step in the plan to the goal. That next step may lead to more questions, which starts this virtuous cycle of correspondence.

Meeting preparation: Context, objectives, and materials

If the correspondence escalates to a meeting, the next generous thing is to prepare for the meeting. Presumably, the meeting is happening because all parties with benefit from a real-time discussion. So there is an inherent value to the meeting. This value will be delivered in the meeting. Preparation ensures that generosity, maximizing the value for everyone while limiting the commitment and time investment required from the participants. Preparation breaks down into three parts: context, objectives, and supporting materials.

Context makes sure that everyone comes to the conversation with the same fact base. Similar to a business school case study, the context should be just enough material that everyone in the room can participate in the meeting. It also explains why everyone in the meeting is there and gets them to think about what benefit they will receive from the meeting. This can be done formally in a slide. It also can be done informally as introductions. It really depends on the meeting, but in every meeting, context explains sets up the value of the meeting.

Objectives affirm why the meeting is happening and what value it brings. Too often this is assumed. When it is assumed and not stated, it can lead to miscommunication, which could really hurt everyone going to the meeting. This is ridiculous because the meeting was agreed to because it was thought to be mutually beneficial. This will be covered more in-depth in a later section, but objectives lead to an ask, which determines the outcome of the meeting. Success of the meeting is not determined by the outcome as much as it is determined by the impression of the meeting. If people walk away from the meeting happy, despite a suboptimal outcome, the meeting was still a success. This derails when the objectives of the meeting misrepresent the ask from the meeting. All parties came to the meeting to achieve something. It is critical to make sure everyone knows what that something is, as stated as a set of objectives.

Materials do multiple things to limit the scope. First, it lays out the plan for the meeting. Next, it creates exhibits of evidence for the discussion. Last, it reinforces that the discussion is about a specific topic not a specific person, removing inappropriate emotion from the conversation. Having a plan with corresponding exhibits keeps the meeting and discussion efficient. It does not mandate rigidity, but rather, instill a framework that guarantees some value for all attendees. If a more valuable issue comes up, adapt. Do not keep a plan for the sake of a plan. However, adaptability is not an excuse to lack a plan that ensures everyone gets value from a meeting. Materials ensure there will be some value in the meeting for everyone.

Removing emotion from a meeting is critical because emotion can totally derail the value for anyone in the meeting. If one person is too passionate, the meeting may spend too much time on one topic and exclude others. Having materials helps declare ground rules to bring a conversation back on track without escalating into an over emotional mess. Additionally, if an argument erupts, the exhibits of facts in the materials help keep an argument objective. Pointing at a piece of paper and saying something on the paper is wrong feels much less like a personal attack than saying, “You’re wrong,” when they are saying the same thing.

Good meetings are really hard. It takes a lot of work to care for all the benefits a team will get in a meeting and ensure that those benefits are achieved in a timely manner. Preparation is really the only key to ensure everyone will get value from the meeting, and it instills strategies that limit the mental, emotional, and time investment in the meeting itself.

Meeting attendance: Execute, think, and listen

Attending the meeting is where the value is delivered. So this section is how to maximize the value from the different perspectives of roles in the meeting. For both the facilitator and the participant, there is a balancing act between contributing and making room for contribution. Optimizing this balancing act is how participants and facilitators are generous in the discussion because it maximizes the ROI for everyone in the meeting.

If I am leading a meeting, the preparation is so critical. It keeps me on track. My duty to everyone else as the facilitator of a meeting is to make sure everyone gets the value that brought them to the meeting. If it’s bringing in an expert, the expert has a chance to share their expertise. If it’s a potential customer, the potential customer has an opportunity to buy. If it’s an investor, the investor has an opportunity to invest. If it’s a customer, they can expect the service offered. Finally, I need to ensure that I get the value that I need from the meeting. Whoever facilitates the conversation tries to ensure everyone, including themselves, gets the value from the meeting that is appropriate to them.

If I am participating in a meeting, it’s my responsibility to deliver the value that I offered to everyone else. It’s the facilitator’s job to make sure I get value out of the conversation. It’s my job, along with all the other participants, to offer something useful or interesting. This does not just mean sharing my own perspectives and expertise, but also creating the negative space for others to share their own perspectives and expertise. The discipline to be direct and the boundaries set that create space for other people to share, makes each word I say more valuable. This limits the investment from everyone else for the value offered, maximizing the engagement ROI.

There are two roles in a meeting: facilitator and participant. The facilitator ensures everyone will receive value from the conversation. The participants maximize the value for each other. Being efficient in the role assigned to you is how you maximize generosity and get the most value from the meeting.

The ask: Be clear and definitive

The ask is the critical conclusion to any meeting. Creating an ask is hard because it is the time people are most vulnerable. The response to the ask is tells whether the outcome from the meeting leads to more or stops. If the outcome is that the discussion concludes, this is not a bad outcome. It is just a reflection of circumstance. Good or bad is determined by how everyone feels walking away from the meeting. These distinctions are so nuanced, it is critical to be clear and precise in this part of a meeting because it will minimize the mental and emotional investment and prevent the value of the meeting from turning negative.

Making an ask needs to be specific. It needs to narrow down to a yes or no response. This ensures clarity. Open-ended questions may follow an ask for clarification, but they are not the ask itself. Beyond being specific in an anticipated response, the terms of the ask also need to be specific. It is asking someone else to participate in an uncertain, delayed gratification. The best example for this is the ask at the end of a pitch meeting: “Do you want to invest?” Before this ask, define the specific terms that you want to offer immediately. The goal is to understand what terms an investor will invest. So anything but an unconditional “Yes,” is a “No.”

If an investor says, “Yes, but on different terms,” it’s a “No.” The investor now countered with their own ask. A safe way to think about this is that each ask has its own meeting. So if there is a new ask from the investor, then there should be a new meeting. The new meeting can be short-circuited with extra preparation by hashing out different terms to different responses. However, if this extra preparation has not occurred, then it’s reasonable to ask for another meeting to discuss the new terms. If this request is denied, then the answer really is a, “No.”

Similarly, answering an ask needs to strive for clarity. This is where an issue often comes up because messages get mixed in the scenario above. Saying, “Yes, but on different terms,” really means, “No, I am not interested in investing on those terms. If you are open to different terms, then I may be interested in investing. Luckily, I know the terms I want.” There is no reason to not have this clarity because clarity ensures authenticity.

Authenticity is a dangerous premise in the whole act of giving or offering any kind of value. It’s really hard to fake providing value. However, it’s really easy to fake the authentic intentions behind providing that value. When people fake their authenticity, it is in a move to take advantage of another person, intentionally or unintentionally. So faking authenticity or coming across as inauthentic is dangerous. Rightfully, people get skeptical when they sense an offer as inauthentic. This leads to distrust and maybe even resentment where all parties are worse off. So clarity of terms and intention are of utmost importance in this circumstance.

The ask of any meeting is the most vulnerable point because it’s the point where everyone reaches an outcome. Regardless of the actual outcome, if handled poorly, this is the point where feelings are hurt and grudges form. Success is that everyone walks away with some benefit from the meeting. Clarity in the ask and the answer is the only way to keep the meeting generous for all.


Over my career, I realized that generosity is really critical to any kind of success. Generosity is not just offering something of value, but offering something of value where it requires relatively little investment from someone else. It’s not just value, but a high ROI for another person. The gratitude the other person feels, leads to reciprocation. It is impossible to see in real-time, the long-term benefits of this virtuous cycle. However, if we notice the details in our daily interactions, it is possible to see how we can be generous everyday.

I am consistently surprised on how the small acts of generosity translated into great things that compound over time. Yes, it’s helped in my career. However, even small things that I never considered, also had incredible results. When I quit playing the drums, I sold a drum kit to a childhood neighbor. I saw that neighbor this weekend for the first time in years. The first thing he did was thank me? Selling him that drum kit set him on the path to become a professional drummer! It was wild. Generosity is not just about the absolute value. Small acts can have a huge impact. It’s about sharing some value that is easy to obtain. That’s what people remember and creates a virtuous cycle of success.

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