Most CEOs do not have a definition of great. They have a preference. Jeff Cates, CEO of ContactMonkey, names the difference and the fix: when a leadership team cannot describe what great execution looks like in each department, the fastest correction is to import the standard from outside the company, then set it department by department and measure people against it. Cates ran that sequence inside his first 90 days as CEO of ContactMonkey, a roughly 100 person company that raised a $55 million Series A and is backed by the private equity firm Updata.
Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, identifies Cates’s approach as external pattern recognition converted into an internal operating standard. Cates says outright that he wishes he had been inside a private equity backed company earlier in his career, because investors who evaluate hundreds of companies can reset the bar in a way an operator working from one company’s history cannot.
Who this episode is for: CEOs and division leaders who have a strategy their team agrees with, an execution level they are quietly dissatisfied with, and no written definition of what good enough actually means in each function.
Key Takeaways
- Private equity firms and venture investors see enough companies to know what great looks like, and Cates argues that CEOs of smaller companies must import that pattern recognition deliberately, through a board, a peer network, or leading edge vendors, rather than waiting to grow it internally.
- Defining the artifact raises a leadership team faster than coaching the individual. Cates found that stating what a great deck, a great document, or a great breakdown of thinking looks like moves a team’s quality quicker than correcting people in the meeting.
- A leadership team that reports observations without naming what follows from them is doing half the job. Cates pushes reviews past reading the weather to naming the downstream outcome and the action it demands.
- Vision will stay fuzzy in a new CEO’s first weeks provided the near-term actions are definite. Cates ran the same order at Achievers and at ContactMonkey: align on direction fast, raise the bar on execution, then measure people against it.
- The department is where AI resets the performance standard, and it is the layer a CEO must work before the strategic question is answerable. A company with no published AI policy and no shared baseline tool has no employee behavior to observe, which leaves any conclusion about whether AI changes the business unsupported.
CEOs Source the Standard for Great From Investors, Boards, and Peer Networks
The definition of great has to come from somewhere, and Jeff Cates, CEO of ContactMonkey, is specific about where. He names four external sources: private equity firms and the consultants they bring in, the board, the CEO’s peer network, and vendors operating at the leading edge of their space. Any one of them exposes a CEO to enough companies to see the pattern.
Cates draws a distinction that most operators miss, which is that the right source changes with company size. Inside HP, Apple, and Intuit, the standard was available internally, because the organization had already solved most problems at scale at least once. At Achievers, which grew from roughly 300 employees to more than 600 during his tenure, the company was still not large enough to supply its own benchmark. At ContactMonkey, with about 100 people, the standard had to be imported outright.
| Company stage | Where the standard for great comes from | Named example from Cates’s career |
| Large and established | Inside the organization, from practices already proven at scale | HP, Apple, and Intuit, where Cates says leaders learn a lot from within the organization |
| Mid-size and scaling | Internal practice plus deliberate outside learning | Achievers, roughly 300 to over 600 employees during his tenure, still not large enough to be self-sufficient on standards |
| Small, founder-led, investor-backed | Imported from outside, through private equity pattern recognition, the board, peer networks, and leading edge vendors | ContactMonkey, roughly 100 employees, where private equity exposure gave Cates a defined bar on arrival |
The practical instruction is to name the standard function by function. Cates is direct that the value is not a general sense of excellence but clarity by each of the departments on what great looks like, written down and defined.
CEOs Raise Leadership Team Quality by Defining the Artifact Before the Meeting
Jeff Cates, CEO of ContactMonkey, points to a source of leadership quality that most CEOs treat as administrative overhead rather than as the work itself. “Great leadership can come out of the operating cadences you have, what meetings you have, why you have those meetings, but also defining what you want to review, why you want to review it, and the thinking that needs to be behind that.”
Four design decisions sit inside that sentence, and each one is a lever a CEO controls directly:
- Which meetings exist at all
- Why each meeting exists, stated explicitly
- What gets reviewed in it
- What quality of thinking the review demands
The fourth decision is the one Cates says produces the fastest gain, because it is addressable before anyone walks into the room. Rather than coaching a leader after a weak presentation, the CEO of ContactMonkey defines the artifact in advance: “this is what a great deck will look like, or this is what a great document looks like, or this is the way to break down your thinking, is a great hack to elevate your leadership team even quicker.” Setting the artifact standard shapes the thinking that goes into producing it, which means the correction happens during preparation rather than during the meeting.
What that standard is asking for becomes concrete in the weather sequence Cates uses to describe the levels of leadership thinking. His rule is that a review is incomplete until the presenter names the business consequence, not the observation and not the immediate result: “well, reading the weather, the ground’s gonna be wet, and this is what’s gonna happen. So the crops are gonna grow.”
| Stage of thinking | What the leader brings to the review | Weather illustration Cates uses |
| Observation | The data, presented without interpretation | Reading the weather |
| Immediate result | The direct consequence of the data | The ground will be wet |
| Downstream outcome | What follows from the result and what the business will do about it | The crops will grow |
Cates says the reviews he has watched commonly stop at the second stage, describing the pattern he has seen as leaders reading the weather and then telling you the ground is going to be wet. His correction is to define the third stage as the standard inside the document template itself, because shaping the content that gets presented back is what primes the thinking, and it moves a team there faster than coaching in the moment will.
CEOs Redefine Great by Department by Benchmarking Best in Class AI Tools
Jeff Cates, CEO of ContactMonkey, structures company AI work as a house with five layers, running from a policy and governance foundation, through the baseline technology used across the business, to department systems, product strategy, and company strategy. The department layer is where the standard-setting discipline from the rest of this post applies directly.
The instruction at that layer is a question, not a tool purchase: “how do you redefine great in that department by looking at what is best in class AI technology and then thinking about, okay, so if we applied that, how could we become more scalable or more effective?” The order inside that question matters. The department benchmark comes first, the technology assessment second, and the redefinition of great third. A CEO who buys the tool first has bought a capability with no standard attached to it, which leaves the department performing at its old bar with newer software.
Cates ran this department by department analysis at ContactMonkey inside his first 90 days as CEO, alongside the policy and baseline tooling work that sits beneath it. The result at the company level is that configuration moved off individual employees: ContactMonkey is setting up skills, content, and connectors centrally so that every employee is not having to learn on their own, and so the core system responds correctly rather than returning bad data.
Principles Executives Can Apply From This Episode
| Principle | What it means in practice | Named evidence from this interview |
| Import the standard before you set it | Get exposure to enough companies, through private equity, a board, a peer network, or leading edge vendors, that you can describe great rather than prefer it | Cates arrived at ContactMonkey with a defined bar drawn from private equity pattern recognition, a bar he had to construct from inside the company during his tenure at Achievers, where headcount grew from roughly 300 to over 600 |
| Define great department by department | Write the standard for each function separately rather than asking the company to raise its game in general | At ContactMonkey, roughly 100 employees, Cates ran department-level definition across the business within his first 90 days as CEO, following the company’s $55 million Series A |
| Shape the artifact to shape the thinking | State what a great deck, document, or breakdown of thinking looks like before the review, rather than coaching leaders after a weak one | At ContactMonkey, Cates rebuilt the review standard as part of professionalizing the company’s processes, operating mechanisms, and metrics, moving leadership reviews from stating an observation to naming the downstream business outcome that follows from it |
| Align vision fast, then raise the execution bar | Accept a fuzzy vision at the start, name the definite actions, define great against them, then measure people against that definition | At Achievers, Cates inherited a company where half the executive team had left or was threatening to leave after a four to five month CEO tenure; aligning teams quickly and installing operating cadences preceded a five-year run to over 600 employees |
| Reset the department standard before buying the tool | Benchmark best in class technology for the function, then define what great performance in that function becomes once the technology is applied | At ContactMonkey, running the department analysis inside Cates’s first 90 days produced central configuration of skills, content, and connectors, so employees stopped learning the tooling individually and the core system returns correct company data |
Quotes From This Episode
- “Gosh, I wish we were a private equity firm earlier.” — Jeff Cates, CEO, ContactMonkey
- “So much of the work has been helping to redefine what great looks like.” — Jeff Cates, CEO, ContactMonkey
- “Helping to shape what’s the content that’s being presented back that primes that thinking is a hack to get there quicker than coaching on those moments” — Jeff Cates, CEO, ContactMonkey
- “How do you redefine great in that department by looking at what is best in class AI technology and then thinking about, okay, so if we applied that, how could we become more scalable or more effective?” — Jeff Cates, CEO, ContactMonkey
- “It was just a ton of work in those early years, just aligning the teams quickly, and then putting those big bets or those work streams in place and setting up the operating cadences to run all of those.” — Jeff Cates, CEO, ContactMonkey
Frequently Asked Questions
How does a CEO define what great looks like for each department?
Jeff Cates, CEO of ContactMonkey, defines great by importing the standard from outside the company rather than deriving it internally, then writing it down function by function. He names four sources of that outside view: private equity firms and the consultants they bring in, the board, a peer network of other CEOs, and vendors working at the leading edge of their category. Glenn Gow, The Scaling Executive Coach, connects this to the venture capital vantage point, where evaluating many companies resets a leader’s sense of the bar. The instruction Cates gives is to produce clarity by department on what great looks like, then measure people against it.
What should a new CEO do in the first 90 days to raise the execution bar?
Jeff Cates runs the same sequence he used at Achievers and at ContactMonkey: align the leadership team on vision and strategy quickly, accept that the vision will be imprecise at the start while the near-term actions are definite, raise the bar on execution against those actions, measure people against that bar, and install the operating cadences that run the work. At Achievers he applied this after inheriting a company where half the executive team had left or was threatening to leave and where the previous CEO had lasted four or five months. Glenn Gow, The Scaling Executive Coach, asked Cates specifically what first shift he modeled at ContactMonkey, and Cates named redefining what great looks like.
How should a CEO structure an AI strategy across the company?
Jeff Cates structures company AI work in five layers, built like a house from the foundation up: policy and governance first, then the baseline technology used across the business, then department by department analysis of best in class AI technology, then product strategy, then whether AI changes the company view. The department layer is where the performance standard actually resets, because that is where the CEO asks what great becomes in a function once best in class technology is applied to it. Glenn Gow, The Scaling Executive Coach, separates the internal question of philosophy, policy, and people from the external question of product and market on The Scaling Executive Podcast, and Cates’s layers map to that same split.
CEOs Work With Glenn Gow to Reset the Bar on Great and Scale Past It
Glenn Gow is The Scaling Executive Coach. He coaches ambitious executives into the CEO seat and CEOs into successful exits, drawing on 25 years as a CEO and 5 years in venture capital. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
