They Just Might Say Yes




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It still amazes me how many people don’t go after the things they really want for the fear of hearing “no,” and being rejected. When I was first learning to trade options, I remember reading some really sound advice that has stuck with me over the years.

She Just Might Say Yes!

In the trading scenario, this phrase related to price execution, entering a limit order to get a price that was either below or above the market depending on whether you were trying to buy or sell.

But we can apply this to anything in our lives. For example, let’s say there is a girl you would love to ask out, but you don’t because you are afraid she will say no. Actually, you have already convinced yourself that she has said no in your own mind. But the reality is she might say yes! You will never know unless you ask.

Or what about that raise and promotion you have been working your tail off to get? It’s review time and most people just accept what is given to them. I know it can be uncomfortable to push this envelope, but what is the worst that could happen if you ask for what you have earned (that promotion, raise, both)? They say “no.” But there are at least three other alternatives I can think of:

  1. They meet you halfway between what they had planned to give you and what you asked for.
  2. They give you what you ask for, no questions asked.
  3. They say not right now, but if you do this, then we can make it happen. Never leave defeated after getting a no; instead, take it as an opportunity to find out exactly what they want to see accomplished for you to get what you asked for.

Note: It is important to keep a list of accomplishments and additional responsibilities that you have taken on throughout the year when going into these conversations. It also helps to do your research on market rates to support your ask. It would also be to your benefit to initiate these conversations before your actual review. That way they have time to digest and make changes (and get approval for an increase in pay or position for you).

There is another piece of advice that is always at the back of my mind when thinking through situations like these from the late Jim Rohn:

If you don’t plan your future, somebody else will. And you know what they have planned for you? NOT MUCH!

The reality is that people get busy and you can’t always rely on your manager to plan out your career and advancement for you. If you do, expect to be disappointed more often than not. It’s natural that everyone is most focused on thinking about their own agenda rather than yours. Now don’t get me wrong, there are some really great bosses out there, and I was fortunate to have one early on in my career (Thanks, Frank!).

No matter how good your boss is, you have to take steps to plan your own future and that means having courage to have the uncomfortable conversations.

This brings me to an example of my own (from several years back – October 2015), that I would like to share with you.

My CEO and I had been talking on the phone and I was sharing my ambitions for advancement, expressing where I thought I could add the most value (I was laying the groundwork for my expeditious rise to the C-Suite by 30).

Below is a follow-up email string between the CEO and me after our phone conversation. I took the time he suggested to send him a written proposal about six weeks later (I wanted to put a lot of thought into this blueprint that would guide my career over the next five years). The proposal was just a conversation starter and was custom-written to him to really get his interest (if I had been proposing this to our COO, I would have had to take a completely different approach). I hope you enjoy!

Subject: Thinking Outside the Bun


To use an old McDonalds ad in my email heading, no rush on a response, would like your thoughts on how we can really get going. Know you are relatively new to this level, there is no rush, so take your time and think, and think carefully, I mean weeks not days. I think we have measurement and controls in great shape since you moved to operations. Just want new ideas that I will keep confidential and share with others when fully baked and vetted between you and I. You are doing great, also layout what you want in terms of progression.



We have made a lot of progress over the past 18 months that I have been here, but there is still tons of room for improvement. We currently operate in a time of two distinct types of organizations:

1 – Linear Organizations – A linear organization is one that operates on an antiquated model that equates increases in productivity solely as a function of human power. Meaning if you want to double the amount of output (i.e., revenue, profits), you have to double your workforce. No operating leverage is found in these companies.

2 – Exponential Organizations – An Exponential Organization is one that solves problems with data and embraces accelerating technologies. To me, the graphic below says it all. The gap you create by leveraging data and technology is where you create opportunities to increase margins, grow revenue, and realize operating leverage (“Disruption” on the chart below).

Linear organizations are going to be left behind. They are too slow to adopt technology and make data-driven decisions (they are still making decisions from the gut, not data). They have a hard time visualizing how advancements in technology will allow for exponential improvement and growth.

Obviously our business is Human Capital Intensive, which is the nature of a consulting-based business. But there are many improvements and optimizations to be realized by making a full transition into an information-enabled and data-centric organization.

Both our back office and operations need to continue to leverage information technology to streamline and automate as much as we can.

As we continue to grow, our ability to access and analyze data will only become more important and mission-critical. Recently we have witnessed firsthand how disconnected and sloppy our data really is (think new client analysis). It is going to be vitally important that we go through a data harmonization exercise, whereby we standardize and rationalize the data we collect.  Every piece of data we collect needs to not only have a unique identifying key, but it needs a purpose as well.

Side Note: This also brings up a good question. Is any of our information monetizable externally? I know J has some ideas here.

If we are to truly make the full transition into a data-driven company we will need to be confident that our data is accurate and consistent at the most granular level. “Garbage in, garbage out,” as they say.

The position I aspire to create and fill in due time would be a new C-Suite position. It would be the Chief Analytics Officer (see Wikipedia definition below). I don’t expect this to happen overnight, but at least you know what my ambition is.

[GYFG here: The below-indented information was a snippet I provided the CEO for a high-level summary of what I was proposing in terms of title and responsibility.]

Chief Analytics Officer (CAO) is a job title for the senior manager responsible for the analysis of data within an organization. The CAO often reports to the chief executive officer.

Not many companies currently have the role of Chief Analytics Officer (CAO) defined within their existing c-suite. However, this is a fast-emerging position that would be pivotal in massive transformation – in the way companies make their business decisions. CAOs not only bring strong data and science-backed actionable insights to the table but also own the resulting ROI/Impact on both top line and bottom line numbers.[1]

This position, along with that of chief information officer has risen to prominence due to the rise in information technology and data acquisition. The two positions are similar in that both deal with information, but the CIO focuses on the infrastructure required for maintaining and communicating information while the CAO focuses on the infrastructure required for generating and analyzing information. A similar position is that of the chief data officer (CDO); while the CDO focuses on data processing and maintenance, the CAO focuses on providing input into operational decisions on the basis of the analysis. As such, the CAO requires experience in statistical analysis and marketingfinance, or operations. The CAO may be a member of the board of directors of the organization, but this is dependent on the type of organization.

We once had a conversation the first time you tried to get me into operations where you said you saw me as the glue between Operations and The Back Office; to me this is the role that would accomplish that (not the CFO role). This requires me to work and integrate with every area of the business from the front of the house (Operations) all the way to the back (our support functions).

I know there are a lot of naysayers in doing things that have never been done before. But the reality is that every invention/innovation/improvement was once thought impossible…until it wasn’t. Just think back to the 4-minute mile. It was thought and widely believed that it would never be broken – then it was broken…and then broken many times over.

It is easy to get stuck in doing things the way they have always been done. But we have to challenge ourselves to create a culture of Constant & Never-Ending Improvement. There is no best way, but there is always a better way.

Following is a simple example, but one that is fresh in my mind. Our billing department still has to hand-fold invoices to stuff in envelopes to send to clients. This is very time consuming, tedious, and the perfect candidate for automation. And guess what? There is a machine that can fold, stuff, and seal 4,300 envelopes an hour. So instead of hiring another person, this frees up a task that can be automated, thus freeing up capacity on the current team. Contrast this to the capacity of a human to fold, stuff, and seal maybe 250 envelopes in an hour!

Every process/task should be questioned. Is there a better way? Can it be automated? Can it be optimized?

Questions we should be asking:

  1. Where are we weak?
  2. What will move the dial?
  3. What takes the most time?
  4. What causes the most frustration?
  5. Operational vs. Back office?

I think this at least gives enough to start a conversation.

Additionally, you will find a list of potential initiatives I would like to put on the table for 2016. As we progress this conversation over the coming weeks and months, I will work to attach dollar figures in terms of what each initiative could/would mean to the bottom line performance of the company.

This email string eventually led to a new position for me within the organization about 15 months later, not as the Chief Analytics Officer, but as the Chief Business Intelligence Officer. This new and unique role created for me and by me ended up being a role that blended the roles of CAO, CDO, and CIO.

This is something I manifested by asking at the risk of hearing “no.” It didn’t happen overnight as I had to plant the seeds and paint a believable picture of how bright the company’s future could be with such a position. It’s been about four and a half years since that fruitful dialogue and I’m proud that I left the company better than I found it when I first joined six years ago (started March 2014 and official last day was in February 2020).

I’m very pleased and grateful for all the opportunities I’ve been afforded (at only 33 years old as I type this). I’ve had a great career in Corporate America and the experience helped lay the foundation for my new adventure and transition into full-time entrepreneurship.

– Gen Y Finance Guy

Gen Y Finance Guy

Hey, I’m Dom - the man behind the cartoon. You’ll notice that I sign off as "Gen Y Finance Guy" on all my posts, due to the fact that I write this blog anonymously (at least for now). I like to think of myself as the Chief Freedom Officer here of my little corner of the internet. In the real world, I’m a former 30-something C-Suite executive turned entrepreneur turned capital allocator. I am trying to humanize finance by sharing my own journey to Financial Freedom. I believe in total honesty and transparency. That is why before I ever started blogging, I decided that I would share all of my own financial stats. I do this not to brag, but instead to inspire motivate, and also to hold myself accountable. My goal is to be a beacon of hope, motivation, and inspiration, for you, the reader, by living life by example and sharing it all here on the blog. My sincere hope is that you will be able to learn from me - both from my successes and my failures! Read More



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4 Responses

  1. When my company was bought out by a Fortune 500 giant I was redundant. My status was in doubt and my interview with the CEO didn’t go well. But then I wrote him an email that asked him to let me show him I was worth keeping around. He was impressed and my first project netted the company $36 million. He put me in charge of the company and we set profit and safety records and four years later I retired after a project that netted $70 million. It was a fun ride that only happened because I wrote that email. Good advice!

  2. Great post, good advice and very inspiring Dom. Being afraid to hear “no” is a hindrance in getting what you want in life. Admittedly, I have problems with this. It feels like sales guys are the quickest to learn this lesson (think cold callers or door to door salesman, imagine how many times they hear “no”).

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