A Simple Hack that will Make the Leadership Team of any Company More Successful

Ken Pulverman
9 min readMar 3, 2021

Embrace the Inherent Bias of your Role & Call it Out to Counteract It

Photo Curtesy of Essentia Analytics

Do you ever wonder why most CEOs come from either Sales or Product organizations? Most people think it is because they can either get big deals done or they know the product inside and out. Both of these skills certainly don’t hurt, but my take is that they are specifically selected by boards because they are the most visibly committed believers. These two functions are the paid zealots for whatever the company does. As a steward of the funding of the company, a board always wants an optimistic, can-do attitude. But money at the core of the interaction can certainly get in the way, as hard things do take time, but sources of funding are generally not patient. Thus, what the board wants and what the board needs might actually be different. In the end, it is the dynamic and effort of the whole team that makes a company a success.

Extending the discussion to the entire executive team, bias is inherent in every CXO role, and if we can recognize this, we can own it, and we can be more effective. Let’s dig into the engrained biases for each of the senior leaders in a company and explain why this bias is both a source of their strength and a handicap.

CPO — The CPO, by virtue of the nature of the role, has to be an eternal optimist. Of course, the product does what it is expected to do. Of course, we are headed in the right direction. Of course, our product plans internalize the needs of the customer. Of course, our baby is beautiful. This optimism is a source of great strength in making hard things happen. When work at the coal face gets particularly hard, this person’s underlying optimism can pull them & the company through. Their inherent belief in their plans is also uniquely credible in front of the customer. Everyone loves a cogent zealot when you need inspiration. The downside of these convictions is it can be hard to hear when your baby did something wrong or someone called it ugly. A big challenge with this role is understanding fitness for purpose at each stage of the company. Do we really have an MVP? How much more do we need to do to have a whole product? How much do I need to support product-led growth to field a complete offering? If this person buys into their own beliefs and rhetoric unflinchingly without letting countervailing views in, problems do occur. Customer needs get pushed aside. Product-market fit takes longer than expected, etc.

CTO — The CTO is generally a pessimist. This person knows what great technology looks like and quietly balks when the CEO’s and CPO’s plans clearly aren’t very ambitious. This person’s bias is to build great things juxtaposed to the understanding that their organization’s capabilities have certain limitations. CTOs also want to time to build great things and sometimes their timeline extends far beyond the market, competition, or available funding. CTOs can therefore back the organization into somewhat of a corner where they may be right that the plan is not very ambitious, but also pessimistic that they can get it done in a timeframe that is meaningful to the business. Often a quieter voice on the team, the CTO, if the other C staff members get up to their elbows in what he or she is seeing, can guide the team in identifying what not to do to put the most important priorities back on the table. Often times the CTO has a unique vantage point to recognize that the company is building functionality for two competing business plans. Here in the CTO’s organization, more than anywhere else in a business, the true opportunity cost of executing one action vs. another reveals itself if it is carefully allowed to surface.

CCO — The Chief Customer Officer is generally the steward of existing customer satisfaction and recurring revenue. As such, there is built-in bias to the just that says “we aren’t doing enough for the customers” and “we aren’t improving fast enough,” a pessimistic position. Great Chief Customer Officers balance this tendency with the experience interpret what the company should be doing at this stage of their growth with the knowledge that the shiny house on the hill will take some time to build. Impatient CCOs can become the ultimate pessimists by going native with the views of some existing customers. They can paint a story of gloom and doom if we don’t do x, y, and z when a holistic view might reveal that what a given customer wants may not be a part of the company’s future path at all.

CFO — The CFOs are paid skeptics by the very nature of their role. Their bias is so often that we are spending too much, hiring too fast, etc. etc. They are at odds with marketing which often has the highest discretionary budget. They have an inherent belief that sales expenses are out of control. They never think we are charging enough. Behind these beliefs are generally great training and experience that helps a company uncover problems before they are acute. Unchecked, though, their views can put the brakes on too hard for a growing venture.

CHRO — The Chief Human Resources Officers are squarely optimists generally believing the team is great & can do amazing things. In their fight for the rights of the team, though, they are constantly tempted to go native as it is a very popular place to be. This challenge is on full display in the current fad title for this area — VP, People. In reality, supporting a growing organization optimally means making many hard and unpopular decisions over time. Teams and management need to be upgraded, raises and benefits must be sensible to ensure the viability of the company, goals must be aggressive to get maximum performance. The seduction of the popular position in this role is very strong and takes extreme will power and forcefulness to overcome. The CHRO constantly has to overcome this bias to be a strong value add to a growing business where hard and unpopular choices at the right time produce needed inflection points that contribute significantly to success.

CMO — The CMO is a split personality. To the external market, the CMO, needs to be a complete optimist and paint a picture that the only way is up and that growth is almost assured, provided this is not too far from the truth. Internally, the CMO can be the ultimate pessimist as this person has studied what the customer wants, knows which segments you need to sell to first to be successful, and, in general, knows exactly what you have. If this gap is too large, the CMO can be a noisy advocate for the customer. This seeming Jekyll and Hyde dichotomy is not well understood by the rest of the team and the CMO can be seen as a “non-believer” at times. However, this is actually part of the role in an effort to get the company to actually be its best self.

CRO — The CRO is an inherent optimist with a dash of pessimist mixed in. To the customer, he or she needs to convey that the company’s solution is better than sliced bread. To the sales team, he or she needs to set aggressive goals and believe they can happen brushing away any obvious obstacles. To the management team and the board, the sales leader needs to convey skepticism, but very subtly. To the casual observer, it might be so subtle that it isn’t that obvious. The sales leader needs to signal the challenges of a junior team, lack of sales enablement, a convoluted story, or clear product gaps in advance. Should a lofty goal be missed, he or she can amplify those challenges. The sales leader lives daily at the intersection between a can-do attitude and trumpeting the need for a successful and repeatable process making them an ideal commercial champion and potential future CEO.

CEO — the CEO role is the hardest job of the lot. There is almost no one cheering for you, you have no peers in the company, and anything that doesn’t naturally fall on one of the CXOs ends up on your plate. Having said that, it is also clearly the most rewarding as external doors open up easily to you, the board provides more guidance than direct management, and the position is almost guaranteed to be the most financially rewarding. Having worked with numerous CEOs and consulted with many others, whether they come from product, sales, or elsewhere they have to be a paid cheerleader for the company. CEOs that ever go dark in their views piss off boards as they are expected to be a booster who firmly believes that the investment the board has committed is being well spent in route to a great outcome. The downside of this unbridled optimism is that a CEO can become a “good news Charlie,” preferring to hear and only making time for good news as so many people want the CEO to deal with their bad news or make an unpopular decision for them. Unfortunately, the best decisions the company can make may be buried in the bad news.

What I find executives teams fail to do which is a relatively simple hack is to put the biases inherent to their role on the table. If we fully embraced that these biases exist, we could come to better agreements by calling out these biases directly and asking if they are influencing a view on a decision or not.

CCO, are you so strongly advocating this solution because you know this is a customer we will certainly lose and cannot live without or have you gone a bit native and are not seeing the constraints on our resources properly?

CHRO, are you objecting to a freeze on raises because you truly believe it will impact the business or do you not want to be THE face or one of the key faces making such an unpopular decision?

CMO, are you being a pain in the ass about product progress because you truly believe it will impact our potential reach and results or is your bias creeping in and making your judgement harsher than is truly needs to be to achieve our goals?

If we allowed ourselves to essentially put our cards on the table including the natural biases of our roles, we would assuredly make better decisions and make them faster. We would also cut through a lot of crap, resentment, and friction that occurs when what should be said remains unsaid. Executive team consultants often talk about creating a space for frank dialogue. They may also sometimes mention bias. What I have never heard them do though, is call out the inherent biases of each key role an insist that they be on the table to create that safe space.

What is important to always realize is that each of these leaders is in this seat because they have risen to the top of their professions. They come to work to do a great job. The temptation, though, of biases that are essentially built into their roles can, therefore, often put them at cross purposes with their colleagues almost by design. Great CEOs get this and try to absorb both the optimistic & aggressive with the pessimistic & conservative views before making an informed decision. What I am advocating here is that this pressure of balancing all of these forces should not be exclusively on the shoulders of the CEO. The entire executive team needs to learn to check the biases of their silo at the door. Better still, each person calls their own biases. And best, each person gives permission to their colleagues to call their biases out. Understanding and embracing this inherent friction, if fully exposed and managed with a minimum amount of grief, simply leads to better decisions and more successful companies. The delicate dance of making a company successful is the effective balancing of these competing forces. Leaving it all up to the CEO to manage is both unrealistic and haircuts your company’s potential.

How do these inherent biases that I have seen as patterns square with your experience? I’d love to hear your take as the differences you’ve seen would be illuminating to me and anyone interested enough in this subject to read this far.

Ken Pulverman is a five time marketing & product leader whose work has driven two acquisitions, one IPO, and a promising D series work in progress. Ken consults on the topics of strategy, marketing, and product to primarily tech companies under his brand SageCMO.

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Ken Pulverman

Executive | CMO | Product Leader | Strategy Expert | Digital Marketer | Applauded Writer | Awarded Product Manager