I won’t be holding the subscriber’s office hours at 8 am tomorrow so I can attend an analyst’s event. Expect an article from that event at the end of next week. Significant AI developments are coming from unexpected companies. I’ll continue covering the gaps for the community.
A key to career success is figuring out how to get around the word “no.” It's good interpersonal etiquette to stop asking when someone says “no.” It's bad business form. That's counterintuitive, especially if you come from a technical background. Most worry about coming off as annoying or being seen as self-centered.
I’ll start this article by explaining how we become comfortable with hearing “no” and how to prepare people to say “yes.” I had a manager tell me a difficult truth early in my career. The framing helped me get beyond the first phase of managing rejection: fear.
The Rejection Management Cycle
Dealing with rejection goes through 4 phases. In the first phase, we're too afraid to ask. Getting rejected is deeply personal, so we avoid any situation where it could happen. My manager said something profound.
You’re already being told ‘no.’ Every time you don’t ask, you don’t get. The rejection is happening, so not asking is a form of denial. If I didn’t hear the word, it didn’t happen. The outcome is still a rejection, and the reality is they said “no.”
Getting beyond phase 1 happens when we begin to ask and stop taking rejection personally in a professional setting. In the beginning, we get a lot of “no.” We must learn to formulate the request properly and overcome objections.
In the second phase, we learn to be persuasive. Entry-level sales talks about trying to find ways to “yes.” For people in the data field, data is our way to get to “yes.” We provide supporting evidence and hope the person on the other side of the table makes a good decision. It's frustrating when we realize often they don't.
That leads us to the third phase: attempting to control as much as possible. If we control all the pieces, we're in charge of yes and no. Unfortunately, that only works for so long. Eventually, we realize collaboration is the only way forward in an enterprise setting. We must find ways to lead people to a good decision when we don't have any authority over them.
The fourth phase is setting up a yes before we ask. Avoiding the no upfront requires new skills. I talked about a shorter version of this framework on LinkedIn, and it brought up a subscriber question. What happens when we're going for a really big ask?
There will be resistance, and it will take work to get approval. Phases one through three won’t succeed; we must go straight to four. In this article, I will explain how that works.
We will prepare our audience to say yes, even though this is a very large ask. I will break the concept into steps and make it simple to understand. I'll present a framework allowing you to do the same thing in your circumstances and with your big asks.
Never Ask For Everything Upfront
A misconception holds most people back from finding a way around rejections. We assume if we're doing a big ask, we must put it all out there from the very beginning. The more we ask for, the harder it will be to get approval. That’s what makes a big ask so daunting.
Good news. You don't have to ask for everything all at once, and it's often not a good idea to. Big asks are more successful if they are broken into phases or parts. The first part of the ask should be the smallest.
I break it down by deliverables because deliverables connect to value creation. Everything comes at a cost, and the business has finite resources. Big asks get turned down when senior leaders don’t see the justification—as with my AI Product Management frameworks, delivering value incrementally on the road to something bigger works best. It meets CEOs’ two needs: quarterly returns to satisfy investors and long-term big opportunities to drive long-term growth.
Going Into The CEO’s Pocket
What we don't realize every time we ask a CEO for something is that we are essentially going into their pocket. We're taking out their wallet, and we are grabbing cash. Would you be OK with that?
We must justify pulling cash out of the company’s cashbox. OpenAI’s CEO crisis provided insight into how senior leaders think. Immediately after Sam Altman was dismissed, OpenAI employees expressed their displeasure about it.
Suddenly, employment offers went out on social media for anyone considering leaving OpenAI. Companies were willing to match salaries and equity sight unseen.
Many people inside those companies said, “I thought we had a hiring freeze!?” Apparently, that hiring freeze was pretty selective. It shows that CEOs will open the cash box if they see dollar signs or significant value to be had.
The secret to getting approval from most CxOs is to make the value obvious. They reject requests for two reasons. They don’t see the value, or they don’t believe the person asking can deliver the value. We focus on proving the value or opportunity is real but overlook the second part.
We need to prove that we can create value equal to this big thing we're asking for. We need to start somewhere if we haven't established a track record of delivering those sorts of large home runs. The first small ask starts a track record of success, establishing enough credibility to ask for more.
Build the first ask around what you can deliver quickly. Deliver, then ask for more. The other benefit of a small ask is career risk. You'll likely lose your job if you fail with a big ask. Failing with a small ask is recoverable.