The Art of the Ask

Mount Ranier

The Lighting of the Beacons” by Howard Shore from “The Lord of the Rings[9]: The Return of the King – The Complete Recordings (Limited Edition) 🎵

This week has gotten me thinking about the art of the ask as demonstrated through commitment.

All decisions are made better when pitched from the perspective of opportunity – If we want to get what we ask for, and we ask for tougher pitches with growth, we have to first demonstrate we are consistent.

Doing What We’ll Say We’ll Do

It is extremely important to me to do what I will say I will do – ideally in the time frame I’ve said I will do it. This is both true in business but also true for me personally.

It is important to me to demonstrate this even when it gets hard, even when tempted with “easy wins” that others would rather chase, and even when dangled with carrots to pause over and over and over to still be committed to the mission of making sure people push to production more to break it a whole lot less and call out what’s blocking that no matter where I am or where I work. Often, it’s people scared to let go.

When it comes to commitment, often I try to find opportunity in existing opportunity while executing on it – for example, if I was planning a trip for a long-time to finally meet someone, finding a way to also align that trip to see other people too. Compound value where you can. I will move mountains to stick to a commitment to prove that I can even when it’s hard to do so…🙂.

Seeing anyone smile in surprise that you actually pulled off what you said you would do when it was hardest in a way that truly demonstrates where your values lie is absolutely worth it. Plans evolve, in life, in business, but as long as you keep the core principles to what you are trying to do, those will show through.

Of all the things I stick with, it’s commitment to what I’ve said I will do that has gotten me the furthest in life. None of us will ever achieve a 100% success rate here, but showing that you are trying and coming extremely close with regards to everything you try to pull off is the marker of who you are.

Pivoting has consequences – and there is a difference between having a willingness to be flexible when it counts and pivoting in a way that is destructive to who you are.

Asking for What You Need

Many when asking for what they need will ask for more than what they need. This can work if you know how to do the “pull back” which is to say – asking for only slightly above what you need within reasonable “market value” (whether that’s a job offer, an enterprise discount, a publishing agreement, or simply calibrating anything at all) and knowing you can pull back to what you actually wanted.

This is an art form learned through lived experiences – I’ve seen some not read the room and ask for an extreme amount of ‘what they need.’ Before we make our asks, consider involving the people who know what those sitting opposite of us can reasonably accomplish. The art of getting what we ask for is knowing what the person in front of us can reasonably give. If we ask without researching – negotiating is a trap. In the worst cases, instantaneously.

Many will also pivot their ask repeatedly while it’s still in discussion. The problem with pivoting too much on what we need is often the person in front of us can only give so much. Pivoting while still in the “ask” in a way that is frequent, glowing and voluminous reveals the diaspora of our commitments through inconsistency. It reveals we are not driving, but being driven.

Constant pivoting becomes what we are known for – instead of stability and commitment.

When we ask for help, often those in front of us are pulling on their networks to help us be successful, grant some of our asks, and try to get as close as possible using the resources they have and within reason. For them to be able to do that they have had to demonstrate consistency – sometimes for years.

Leaders know that consistency is a currency for which bartering without wisdom as the compound interest is a foolish bet. And those who are consistent know that if the person in front of them does not value their consistency that person is a thief, not a mutual fund.

If we want to succeed – we have to demonstrate consistency – that doesn’t mean we can’t have resume gaps. You can absolutely change jobs – But it does mean we have to have a belief system that we live by and are vocal about. It means the topics and missions we care about should be ones we are willing to commit to through years with the right partners- even when times gets tough, and even when people ignore us because it’s hard for them to face the truth in a way that transforms their idea of safety until they no longer can ignore it because the problem is too big. For example, this blog for me, demonstrates I’m not backing down on what I believe with regards to testing in production, pushing to production as fast as humanly possible by removing people in the approval flows, and that creating more failures that are smaller scale as you increase merge count, means you are working towards customers never noticing you’re having them at all.

We have to be willing to plant the gardens to reap what we sow while other shake trees for low hanging fruit. Some will need easy wins for your missions. Let others shake the trees – while you learn how to plant them.

What to Do When We Don’t Get What We Ask For

This famous scene from “The Return of the King” is exceptional demonstration of one way to get what you need.

Something that has always been a challenge for me, but for which I’ve gotten better at, is that when I’ve not gotten what I’ve asked for, and I know where my “need” line stands is to move on.


I remember one of my mentors, she told me “Why are you still chasing this opportunity? You have to let it go. They aren’t there for you.” Recognizing that I was not getting back nearly as much as the effort and patience I was putting in to finally hear a yes and that that was not “normal” for me. In fact, what she was calling out distinctly was that the situation I kept wanting to hear ‘yes’ in was against my own moral compass. I had stepped out of alignment because I was navigating towards a situation that continued to demonstrate inconsistency and pivoting trying to make it work for someone else.

Many when they make their ask, will pitch it and then not move on when they get a ‘no.’ but owning a business taught me that not knowing how to move on and not doing so quickly – not having backup plans – will absolutely lower cash flow. I could quite reasonably see in the business bank account the outcomes of my own choices as a CEO to not move on quick enough to find new opportunities.

If we pivot our asks when we hear ‘no’ and re-ask it 6 different ways hoping for the answer to change it is important to recognize when that ask absolutely is failing for any reason. Commitment must go both ways for as long as it can. If the person in front of us cannot give us what we ask for, we have a few choices.

(1) We can say ‘thank you’ but this will not work for us or (2) We can evaluate the answer they’ve given fully with the context they’ve given and embrace it – going that direction or (3) In exceptional cases, we can use our own resources and systems to subvert expectations but only if we have built them first by demonstrating consistency (Ex. The beacons and “Gondor calls for aid!”).

For example, if a team asks to get put on another team’s roadmap and they say ‘no’ with fiery passion because they do not have time, that team could use their own resources to deliver on what needs to get done and ask for a favor later in return for doing work that benefits everyone. They can also reflect on how they asked it in the first place that would have result in such a strong response on something that could have been perceived as trivial by one party but too large an effort to another – All asks are made better with opportunity.

It is often the person in front of us cannot give us what we are asking for because they either do not see the opportunity or those they are beholden to do not see the opportunity clearly.

And well – if others don’t see the opportunities in our asks, we can choose to walk away. The art of all asks, is coming to the table having demonstrated consistency, knowing the bounds within which our asks will be successful, and a firm visibility to the other party that we believe they are worth our time investment after evaluating if we believe they will demonstrate the same principles in return.

Header Image by Monica Macomber from Unsplash.

[9] This is the ninth clue to the puzzle.