From a Veteran to Tech: The Right Way to Employ the Chief of Staff Role

*Originally published on LinkedIn March 24th, 2019.

I admit it, I’ve already lied to you. There is no “perfect” way to be a Chief of Staff (CoS). The best practices of Chiefs of Staff and how the role is applied most effectively truly does depend on organizational structures, processes, standards, culture, people involved (aka “personalities”), the business model(s) in play, and a whole host of other factors. However, these days more and more tech companies are adopting the practice of utilizing the Chief of Staff role and adding the position to their organizational hierarchies (which is a good thing!) than ever before, and there’s definitely some approaches that I’m qualified to recognize as the WRONG way, because I’m not a newbie to it. This article is really just one man’s opinion. However, I’m a stakeholder in what norms gain traction in the commercial world when it comes to expectations of Leadership roles in organizations, such as for Chiefs of Staff. The Chief of Staff role has been a staple in military organizations for a long time, and I’m lucky to have a great amount of firsthand experience with it.


While I have 15+ years of firsthand experience with military Chiefs of Staff, its important that I clarify the scope of my reference. My military experience is in the Army only, up to the brigade staff level, and the formal military title I am actually referring to is the Executive Officer (XO). On Army Brigade Combat Team (BCT) battalion and brigade level staffs, (one of) the XO’s function(s) is to uphold the role of Chief of Staff, on behalf of the Commander. A military XO and a commercial CEO are not equivalent hierarchical roles within their organizations, in spite of the similar title wording. At the military t/c/b (troop /company /battery) level, the XO role is not quite a CoS yet (because there’s not a large enough staff to necessitate that function), but does serve in the same hierarchy to the Commander and oversees most of the same functional areas of responsibility (within t/c/b scope) as a CoS, usually. For purposes of comparing Army roles to their commercial organizational “equivalents” in this article: Commander=CEO, XO=CoS, Ops Officer = COO, at the BCT battlion (~300-800 personnel) or brigade (~3000-5000 personnel) level.

My opinions are shaped by the Army doctrine I learned during my time in Service and through my experience as a former Signal Troop Commander, twice primary staff as a battalion level Signal Officer and a battalion Logistics Officer, and as a Plans Staff Officer for the Ops Officer (COO) at the brigade level, all within BCT structures. They are also shaped by three years of post-transition additional executive leadership experience in commercial tech ops and services in Denver and the North Bay, California. As a job seeker for the time being, I’ve been interested in some CoS roles and there’s HUGE disparity in how different companies convey their take on the role. Here’s my list of 5 “NO-GO’s” (with feedback on to how to apply CoS “wasta” best) for companies considering adding the position into their organizational leadership structure.

1. The Chief of Staff is part Executive Assistant (EA): NO-GO!

NO-GO! The Chief of Staff is not in any way, shape, or form an Executive Assistant. The CoS is second in Command to their boss. Sure, the CoS should be someone who’s willing to “roll their sleeves up” and be prepared to do tasks at times that just need doing when no one else is around to do it… but don’t you expect everyone in your organization to be that way? I do. The CoS is no more an EA than anyone else in the company that’s not an EA in title and core duties. If you set up your SoW for CoS to include some percentage of EA tasks as part of their main duties, you won’t get the ROI that you could out of having a CoS role in your staff structure. The value of the CoS is a force multiplier from the top leadership level. His or her time and effort should be focused on bridging the tactical and strategic ops and plans, and making them happen just as much as the COO. His or her EA SoW should be no more than the COO’s or any other department head, absolutely. If you have more EA type of task volume than you’re EA(s) can cover, I recommend you figure out a different solution than trying to “hey, you” the CoS with them. Just sayin.

2. The Chief of Staff is the CEO’s “Shadow”: NO-GO!

If you’re not aware, Jeff Bezos, so I’ve heard, calls his CoS “his shadow.” My NO-GO point here is not that a CoS can’t be a “shadow” and be effective; I’ve seen Commanders who also use the “shadow” methodology and apply it very well, just as Jeff Bezos clearly has. However, in my experience its very rare that such a shadow application is best, and it only works well in very specific types of conditions dependent on a bunch of factors (most notably the personalities, operating environment, and mission set at hand). My NO-GO point is that just because Jeff Bezos utilizes the CoS role in that way, doesn’t mean that such is always the best way to employ the CoS role.

In fact, in my experience, more often than not, viewing the CoS as the CEO’s shadow (who’s always by their side) as their standard will short-change the organization from getting the most out of having a CoS. The CoS should be “linked at the hip with the CEO” as a huge part of their role responsibilities in order to be most effective for the organization. However, one of the biggest value adds of the CoS into organizational leadership structure is the ability flex key leaders across time and space simultaneously. If areas of responsibility are apportioned properly between the CoS, COO, and CEO, the organization gains a 50% increase in the ability to flex top level leadership across broad (cross-functional) lines of effort by having added the CoS to the mix than without.

3. The Chief of Staff Manages the CEO’s Calendar: NO-GO!

Please refer back to above regarding EA duties. Depending on workload, I recommend using the same EA (or EA section) for the CoS, COO, and CEO, if possible, for management of each of their individual calendars (among other things). The CoS, CEO, and COO do need to be in-sync with each other at all times, but that doesn’t mean that the CoS is managing other people’s calendars. The COO (department) should set the organization’s operational calendar, which must nest the CEO’s and CoS’s operational/deliverable timelines with the Ops side of the house for best overall organizational synchronization. Do not make the mistake of thinking calendar management and organizational synchronization are one and the same.

The CoS should be tracking the CEO’s calendar obligations day to day because the CoS is always on a “be prepared to” mission to stand in for the CEO as required at any given place or time. The CoS should also be at the table in many (if not most) of the same meetings and engagements as the CEO, just as part of keeping in sync and at the same level of situational awareness as him or her. Therefore, the CoS does have to stay abreast of the CEO’s calendar, but their job isn’t to manage it at a task level; their time is too valuable to the organization to be wasted in this way as a part of their primary duties. Organizations should generally use the lowest cost labor that can accomplish tasks to the expected quality standards for most things, as is the case here.

4. The Chief of Staff Only Has “Soft Power”: NO-GO!

In order to get to the “why” behind my point of view on this topic, I’ll first have to share some prerequisite concepts on how the CoS role fits within the CEO-COO-CoS “trifecta” in military organization staff functional leadership and the operations process. The concepts I’m about to explain are truly the most core which shapes my point of view on how to best utilize the CoS role for peak organizational performance, and are concepts which I am certain could help many corporate organizations function better than they do, if understood and put into practice properly. There’s two very important hard rules which I believe are highly transferable to corporate companies, are fundamentally different from how most non-military organizations view themselves, yet are very well understood by outstanding organizational leaders I’ve had experience with in the Army: 1 – All organizational departments, categorically at the top level, are either a function of “Operations” or “Sustainment.” 2 – ALL departments’ primary function is to support “Operations.”

For purposes of explaining these concepts further I’m going to continue to compare BCT brigade/battalion level military staff alignment to corporate C-Level structures. These same concepts can be applied to companies with VP structure rather than C-Titles, but I’ve found that most organizations I’ve seen creating new CoS roles use C-Level titles at the top level, rather than VPs. Plus, for simplicity it just works better. I’m NOT going to go too far in depth to ALL the ins-and-outs of military staff functions and sections – we could go way into the weeds on that and its not the purpose of this article. But, for those that don’t know, here’s the most prominent functional primary staff departments that are found in BCT battalions and brigades: S1=Personnel, S2=Intel, S3=Operations, S4=Logistics, S6=Signal (IT and Tech). Each of those departments has a primary staff officer who heads them, which is synonymous with a C-Level role. Additionally, there’s other types of specialty head staff roles such as Finance, Public Affairs, Civil Affairs, Legal, and Support Operations, which also correlate to some commercial organizations’ C-level billets.

Concerning the primary staff sections, S2 & S3 combine to comprise overall “Operations.” Personnel, Logistics, and Signal are all grouped as functions of “Sustainment.” Specialty Staff usually mostly fall under the Sustainment umbrella, although some may/do rollup under Ops, depending on the mission set and org type. The purpose of all Sustainment sections is to support Operations. By organizational design (aka MTOE), the COO runs the Operations while the CoS is responsible for Sustainment. When it comes down to brass tacks, the CoS actually outranks the COO and is expected to be able to take over for both the CEO if necessary, and also to be able to take over for the COO if needed (and in certain circumstances by design).

However, the CoS’s role outside of those contingencies is to ensure that the Sustainment staff deliver the necessary outcomes to enable operations to thrive. Since the function of Sustainment is organized around Ops, their activities therefore must deliberately be aligned and synchronized against Ops’s requirements, which is what the CoS ensures. The CoS doesn’t (can’t) do this most effectively through soft power. While technically all staff works for the Commander, the Sustainment staff heads are usually (and most effectively) appointed as direct reports to the CoS. All staff, even the COO and their subordinates, recognize that the CoS is empowered by the CEO directly and never make the mistake of confusing CoS directives as suggestions. A CoS with only “soft power” is not a CoS… he or she is really just a coordinator, not a Chief.

5. Military Use of a CoS Can’t Be Applied to Commercial Companies: NO-GO!

I concede that all the detailed particulars of military staff alignment and operational process standards cannot be exactly applied to non-military organizations. Duh. The mission of the military is unique to its industry. However, you’re (no disrespect) ignorant if you don’t see how well these things can align. I mean, you can’t know if you don’t know… but I do, I’ve seen both sides. Although, I recognize that some of my beliefs would really “disrupt” some old ways of thinking about how departments should best be aligned in commercial organizations. Nonetheless, its also my belief that many organizations could greatly benefit from transformation to the type of organizational hierarchy and process design that I’ll example. No one size fits all, but I’ll give a use case (sort of) that should make great sense to many companies.

All companies (should) have some defined mission. Across the great sphere of companies and commercial industries that are out there, there’s huge disparity between organizations regarding what they define as their “operations” side of the house. Most basically, the company’s mission should define its operations. For ease, let’s generically say you’re a company that provides some product or service. Your operations activities (and departments) should be recognized as those specifically producing and/or delivering the core products or services the company offers.

That’s simple, right? Well, where does the military S2 function fall into your commercial Ops equation? Simple, S2 (Intel) in the military (combined with some special staff – PAO, IO, Psyop, and maybe civil affairs) = sales, business development, and marketing in the commercial world. In the military, Intel provides the operating environment analysis and develops the targets that ops goes after in combat. The special staff I referenced produces the broader public messaging to shape opinions, perceptions, and support for the military mission from the populous. Sales and marketing ops, right?

Putting the Intel section with Ops enables a faster and more effective system of selecting and knocking down targets. From my point of view, recognizing the connected nature of sales & marketing with Ops in in the commercial world is an imperative that many companies simply don’t acknowledge, but should. Aligning them together under the authority (and budget) of one COO has huge benefits when it comes to assessing true raw OPEX, synchronizing sales with production to avoid wastefulness, and closing the gap between customer expectations (that sales and marketing set) with what the organization provides (through its ops). COOs empowered to provide unity of direction over sales, marketing, and the ops side of the house are best positioned to directly affect company growth, efficiency, and the bottom line independently… just like knocking down targets.

Now, back to the CoS and Sustainment functions. As a reminder, every section that is not Ops is a function of Sustainment. In a way, this point of view is comparable to putting them in the category of G&A (or overhead), but properly categorizing everything for accounting purposes is definitely not that cut and dry. In any case, the fruits of their labor ensures that the company can sustain Ops. The CoS’s role is to herd the cats that enable sustained ops, while also serving as a check and balance between the COO and CEO. The CoS manages up to advise CEO on the company’s capabilities (and shortcomings) for personnel, commo (IT and Tech), and logistics (inclusive of finance) that are needed to enable the COO to meet the CEOs goals.

The CoS also manages the COO “laterally” in a way to ensure that Ops is oriented on the objectives the CEO has conveyed, and to reconcile Ops planning to ensure that the requirements to the Sustainment departments are achievable, so that the COO has reliable projections to plan against and rely on. With the organization aligned this way, both the COO and CoS stay in sync with the CEO on the organization’s goals at all times because they both directly report to the CEO. They also stay in sync with each other so that all lines of effort move forward in concert among their subordinate staff. The COO and CoS effectively cover all the work that needs to be done in the organization so fully that the CEO is enabled to circulate freely, spend time on leader development and culture in the company, strategic engagements, and overall quality control and steering of the ship (without having to be in the weeds micromanaging).

Tailoring the Chief of Staff Role for Value Add Commercially

As I said in the beginning, there is no one size fits all solution for how to employ the CoS role best for every organization. However, if you’re contemplating the need and/or value add of adding the role into your organizational leadership hierarchy there are some very important lessons to be learned from the time tested military application of the role. First, ask yourself the question: “What problem are we trying to solve through adding a Chief of Staff?” If what you come up with as answer to that question is that you need someone whose major duties are gate-keeping, calendar management, EA work, but also the ability to sit in meetings on behalf of their boss and pass on information to their bosses subordinates without actually being empowered to enforce their boss’s guidance, then I don’t believe calling that role a “Chief of Staff” is the proper nomenclature. I’d call that role an Assistant or perhaps Deputy role to their boss’s title.

However, if your organization’s problem is that your key leader can’t be everywhere they “need” to be in time and space, that things aren’t working as well as they could across departments and/or silos, you need someone who can operate at that key leader’s level, and your key leader is someone who’s comfortable empowering someone else with their trust and authority to divide and conquer on their behalf, adding a Chief of Staff to the mix may be the right answer. I used the term “key leader” above because the CoS can be employed commercially as a tremendous resource for organizational leaders other than just the CEO. However, the same overall principles apply.

Perhaps your key leader (who might need a CoS) is your company’s CPO, CIO, or even the COO. The need for a CoS should normally only arise when there are a larger numbers of subordinate functional areas, leaders, or high level tasks than can be lead and managed at high quality by the C-leader alone. Remember, the biggest value-add of the CoS is as an enabler and force multiplier for depth and flexibility of top leadership in time and space. Perhaps your C-Leader’s time and attention is more important to be spent externally to the organization with strategic engagements as much as possible: employ the CoS to completely manage and lead the internal staff. Perhaps your C-Leader has 8 subordinate Directors, needs someone who can tag-team the workload, assist them at the vision and strategy level, and serve as their respected “consigliere” of sorts: employ the CoS to divide and conquer using a similar construct to the Ops vs. Sustainment methodology tailored to your organizational dynamics, as this problem set is exactly the type befitting for addition of the role. If employed properly at this level, the CoS can add 100% capability increase to the office of the C-Leader they work for.

Final Thoughts

With such an infinite set of circumstances and variety in the processes, cultures, missions, and organizational designs of commercial organizations today across industries, there’s no one size fits all perfect way to implement the CoS role for the best benefit. However, its important that organizations think through their preconceived notions on the purpose of the role historically, fundamentally analyze the problems they expect the role to solve, and set up the role for success (not failure) by empowering it with the right level of authority to deliver the most bang for the buck. If things aren’t working right and you need more leadership on board to make things happen, putting someone with soft power in the mix isn’t going solve your problem. Do not make the mistake of slapping the CoS title on an EA role, show some respect to the moniker “Chief.”

***I appreciate comments, feedback, and love to learn from the experience of others. What’s your take on this? Don’t be a stranger!

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