security awareness communication

Communication Across the Ranges – Leadership

This is the third of a quick three-part series on how to communicate with the three various types of folks that we have to deal with as technical consultants/geeks-in-residence etc.



Do your homework. This one feels self-explanatory but so many of us forget to do a little background on the company we work for or are engaged with, before talking with leadership. What are the goals of the company? Where is the company focused? How if it performing? What is the strategic viewpoint? What was the last earnings call? All of this information will help you talk with the CEO with considerably more understanding, and will help you frame your conversation much more accurately.

Enter and exit gracefully. Understand that you won’t always get what you want. The CEO has to make a ton of decisions and not all of them are popular, not all of them will be in your favor. Accept it. Be gracious, and work with what you have. Help them to understand the decision tree for all outcomes–and then let them make the informed decision. That is why they are in the position they are in.

Present and discuss strategically. Again understand the company, the focus, and what might be happening with the organization. Don’t second guess: be smart. If it’s a retail client, they are all concerned about Amazon. If it’s manufacturing everyone concerned about IP. If it’s healthcare, living patients come first. Know your client and know what/where their focus is. Keep it short and to the point, but have plenty of backup material to hand out in case questions are forthcoming.

Remember, CEO’s ARE people too. Despite what the media says, they have families, and personal challenges. Treat them as humans. Be understanding and considerate of their time.

Here’s a good exercise. Imagine you have only 30 seconds in an elevator to talk with the CEO about a project. How will you explain it? How will you make them think about it? What can you help them understand? This focus will ultimately help you achieve your goals too. Practice that.


Numbers and metrics: It all comes down to the numbers, and not just the ones you put on your spreadsheet, but the actual final versions that sometimes you forget about. The CFO didn’t. They know not just the estimates but also the final tally AND that ongoing operational cost that might have been neglected. This could be your advantage. Help them by being accurate with numbers: do your research. Do research across your vertical market and help the CFO understand the actual cost, and make sure all those “extras” and operational expenses are accounted for. You get this right a few times and you’ll be amazed how the CFO starts to respect your judgment!

Keep it grounded: The CFO’s seen too many ROIs that promise the riches beyond Avarice, but more often than not the project has failed miserably and ended up in a puddle on the floor. Therefore be realistic, be cautious and put in enough time in research. Then be prepared to explain that to the CFO, at least then they will know what you have done AND why.

The CFO knows legal: A good CFO is able to understand the compliance status with the various government regulations, tax statutes and a heap of other red tape that would suffocate mere mortals. Therefore help them by pitching in with the fiduciary duties that you are aware of within the IT realm. If you have SOX, PCI, HIPAA or any other compliance requirement, become not only an expert in your IT area but also help the finance team by explaining the implications there. That way both of you are now working towards a common goal. You have become a team, and not just a couple of people against a sea of regulations. It is much easier, and more effective, to have conversations when everyone is on the same team!

Did we mention measurable? That’s back to the maturity model we’ve talked about over the years. It’s quick, easy and demonstrable metrics that can be quantified, a number allocated from a technical, compliance and financial standpoint and is available in a single page, handy to read format…so start using it!


This person is often the most difficult to pin down and can also be the most challenging to communicate with. The COO can have a variety of different tasks within an organization ranging from simply the “operations person responsible for production, marketing, R&D and development, etc.” or he/she could be the internal visionary of the CEO (who by definition in many large organizations has to be external “face” of the company.)

However it’s well understood that there’s several different flavors of COO, the notes below should help identify the one you are dealing with AND how to effectively communicate with them:

The executor: This person manages the day to day operations of the business, his/her role is to keep things running at peak. Therefore anything that’s going to cause issues with the operations has to be understood, and that’s your “in”.

The change agent: Strategically placed to ensure a key set of successes or deliverables is met. These are the individuals who are focused on a very specific set of goals. Therefore your role is to help them achieve those goals, align your communications accordingly.

The mentor: For a lot of Silicon Valley organizations the CEO is young and the company is growing at a pace that either is threatening to take over them, or already has. You bring in a seasoned and experienced COO as a mentor, and your communication style takes on one of tutoring; you become the one to help answer the tough questions and to understand the day-to day complexities. You become the one to translate those to the COO so they can readily pass this along to the CEO with minimal modification. You are in essence helping the COO to train the CEO.

The future: Many companies test a potential future CEO by placing them in the role of COO. So as a communicator with that person you are once again the tutor; you are helping them gain the necessary insight into the organization and to understand what/why you are talking with them. Frame your advice to benefit them. Education is key here, but again align the message to the business.

There are other leadership roles within organizations, and this is only a short selection, but hopefully it helps anyone reading this to understand that, yes, you can talk with the C-suite without losing your job, your cool or your friends. You just have to understand them a little better and do your homework first.

Above ALL, remember…

1. Shock and awe sells once, same as FUD. You’ll get your toys if you go in and explain that the sky is falling, but the sky only falls once. Better to go in and demonstrate trends, metrics and explain why you can help their organization from not getting caught up in the mess with realistic, measurable and articulate goals that are sympathetic to the overall direction of the company.

2. That 30-second elevator pitch, think about it, and work on it. You’ll be amazed how often in life it comes in handy, and how it helps sharpen your communication skills.

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