Strategic Thinking for Creative Leaders

While there are many skills that an effective creative leader must have, one of the most important skills is strategic thinking.  Creative leadership is the ability to generate and implement both an effective strategy (culminating the first three creativity steps) and effective solution (culminating in the last four creativity steps).  Creative leadership involves effective skills with visionary thinking, strategic thinking, and ideational thinking (creative leaders are good at generating many ideas).  This essay is explores what constitutes an effective strategy, namely the value of a particular strategy.

Strategy Matrix

Strategy

Strategies can be grouped into four categories based on the potential value of a strategy (“Strategic Value”) and its respective difficulty of implementation (“Implementation Difficulty”).  To start this discussion on strategies, we will start by comparing and contrasting the four categories.

While both Critical and Cumulative strategies have high-strategic value, Critical strategies usually have the highest payoff of all strategies, but are more difficult to implement and, as a result, typically foreclose one or more alternative strategies.  In contrast, Cumulative strategies have good payoffs, but are easier to implement, and generally speaking, do not foreclose other opportunities.  Cumulative strategies often work in combination with other strategies, and thus, have an additive impact when aggregated.  Cumulative strategies have less risk and can pursue so long as they make sense on a cost-benefit basis and profitable Critical strategies have been exhausted.

However, the matrix above isn’t really drawn to scale as Critical strategies can sometimes have many times (if not 1000X) the potential impact (and risk) as Cumulative strategies.   Even within each quadrant, there can be great variations in terms of difficulty of implementation and strategic value so nuanced analysis and rank-ordering is usually a good idea, both across and within quadrants.

Critical, Quagmire, and Disaster strategies are all marked by high Implementation Difficulty.  However, a Critical strategy, if implemented effectively, has high Strategic Value.  What makes a Quagmire so bad is that it has high Implementation Difficulty but low strategic value, even if implemented successfully.  The third alternative – Disaster – is not an initial strategy, but rather the actual result when a Critical strategy fails or is implemented poorly.

Both Cumulative and Distraction strategies are easy to implement and tend to be “additive” in nature with each successfully executed strategy bringing the organizational closer to desired results.  This is because easy-to-implement solutions typically do not foreclose the pursuit of other strategies (pursued sequentially or simultaneously).  Though Distraction strategies may have some value, they are labeled Distractions as they divert attention from Cumulative and Critical strategies (if a Distraction strategy had significant strategic value if would be Cumulative).

Having discussed the four quadrants of strategy, this posting will now explore some particular strategies associated with high-strategic value.

High-Strategic Value Strategies

People

Recruiting and hiring the best people is usually a Critical strategy (because it forecloses the opportunity to hire someone else), though some hires have greater potential to impact an organization than others.  For instance, hiring a new CEO will likely be a Board of Directors most Critical strategy of the year; hiring additional members of the leadership team might still be a Critical strategy.  Hiring a new payroll manager, however, at best is more of a Cumulative strategy as the potential payoff of such strategy is not nearly as high.

One common mistake of organizations is that often over-emphasis resume or technical skills over interpersonal skills, character, and general likeability.  An organization will never be great if employees don’t like the other employees that work there.

In addition to hiring the best people, organizations should be committed to developing their people (through mentoring, training, education, delegation of good assignment, development plans, etc.), doubly so in respect to their current and future leaders and triply so in regards to a few hand-selected Critical leaders.

Sometimes overlooked, though equally important to hiring the best, is actually firing the worst performers in an organization.  Too often leaders put off having honest and frank conversations with a few “bad egg” individuals.  While people should be given some chance to correct behavior, they need not be given many chances.  You cannot overestimate the damage one individual can do to an organization.  Even if they aren’t causing major problems, they are taking a space that could be filled by a problem-free contributor or even a star performer.

By identifying and progressively moving the weakest performers out the organization, the organization strengthens its key assets – its people.  Incidentally, this is why governments are totally inefficient, instead of firing people that should be fired, they give them jobs and pensions.

While the following statements border on flippancy, Mitt Romney’s quote is actually part of the reason he is an effective executive leader:  “I like being able to fire people who provide services to me … You know, if someone doesn’t give me a good service that I need, I want to say, I’m going to go get someone else to provide that service to me.”

Similarly, successful leader Donald Trump’s key catch phrase is appropriately, “you’re fired!”  While good leaders wield their power to fire with tact, judgment, patience, and mercy, they still must do it – that is why they are the leader.  However, the best course is to hire very carefully (as a Critical strategy) and slowly so as to prevent the need for firing.

Resources

Critical or Cumulative strategies usually involve obtaining, preserving, and deploying resources effectively.  Obtaining additional resources is usually an important strategy, which is why college president and politicians must be excellent fund-raisers.  In addition, resources must be obtained regardless of whether they come from within (budget and head count allocations) or without (grants, revenue, contributions) the organization.  The failure to obtain resources can lead to disaster or stagnation within an organization or department.

Likewise, obtaining extra resources, if deployed effectively, can generate “momentum” as discussed below.  In addition, there are situations where acquiring a specific resource at a specific time is of the utmost strategic importance to execution of particular strategy.  For instance, the selection of Vice-President Candidate (a resource) is often the single most important strategy decision in a presidential election because of their ability to sway (for or against) certain voting blocs and thereby win (or lose) certain states.

As Benjamin Franklin would say, “a penny saved is a penny earned.”  Thus, conserving resources is a high pay-off strategy.  One way to conserve resources is by carefully cutting any unnecessary or unhelpful costs.  Another way to indirectly cut costs is by a constant commitment to process improvement.  Process improvement allows organizations to increase their output while decreasing their inputs, thus conserving resources.  As a caveat, in some organizations, being too efficient with your budget actually leads to departmental budget cuts, so you have to be careful if you are department head.

Besides physical resources (people, buildings, computers), there are also intangible resources – time, energy, commitments, morale, etc.   An effective strategy seeks to increase and conserve these types of intangible resources just the same as tangible resources.

Likewise, sometimes the worst “leaks” in an organization is psychic drain due to certain aggravating factors (annoying policies, employees, or the pursuit of Quagmire or Distraction strategies) that need to be alleviated.

Similarly, an effective strategy is always to deploy resources more effectively.  Similar to process improvement, by deploying resources well you can increase output while decreasing inputs.  Take a look at my strategic delegation posting for advice on how to do this more effectively.

If you employ all these strategies regarding obtaining, conserving, and deploying resources effectively, you will (hopefully) find that your organization sudden has a surplus of resources. What then?  Use them on Critical and Cumulative strategies of course!

In fact, it is by careful use of your resources you can pursue multiple strategies simultaneously (not all of them can be Critical however).  In particular, you should deploy them on strategies that will generate momentum throughout the organization, including securing key wins, boosting morale, eliminating bottlenecks or drains, improve relationships with key stakeholders, developing leaders and staff, or generating competitive advantage, etc.

Relationships

Critical or Cumulative strategies often involve improving relationships with key stakeholders, both internal and external.  In addition, even strategies that involve ideas, technology, or other things have important people considerations.  Thus, a key strategy is to identify and to improve relationships with key stakeholders.  These could include key internal leaders, employees, as well as external customers, supporters, and even detractors.   While sometimes you have a specific position that you are advocating, developing relationships ahead-of-time is important practice that will help ensure that you have “the votes”, exactly when you need them.

To accomplish this, an effective strategy is to take the time to meet with and communicate with key stakeholders.  In particular, is wise to spend a lot of time listening (rather than talking) in order to learn about the preferences and interests of the stakeholders.  The more you know about the key stakeholders, the better you can adapt your potential strategy – whatever it be – to the context.  In addition, supporting the (non-controversial) projects and interests of key stakeholders helps build the “goodwill” bank account and often ensures that they will support your (non-controversial) measures in the future as well.

Events & Incidents & Opportunities

Critical or Cumulative strategies often involve handling events, incidents, and opportunities – planned and unplanned – is an important strategy and leadership task.  To draw an unfortunate analogy, the most effective leaders act *somewhat* like politicians during a campaign season – they monitor current events, respond to incidents, seize opportunities, and use social events to move their organizations and their campaigns forward with ruthless efficiency.

For instance, think about Joe Paterno’s failure to manage incidents (allegations of abuse on his staff) decimated much that he accomplished.  In contrast, the textbook example of crisis management is Johnson and Johnson’s management of the cyanide Tylenol incident in the 1980s.  This is where J&J was willing to pull the contaminated Tylenol from the shelf costing some short-term financial pain, though the long-term benefit to its brand were enormous.

Equally important to crisis management, however, is a leader’s ability to spot and capitalize (and create) opportunities.  If executed well, a leader can turn an opportunity in a small or large victory, which generates a leader’s most important (and fickle) resource – organizational momentum.  Anyone who has played on a team that was “on fire” knows the power of momentum.  Likewise, anyone who has spent time on a losing team or organization knows that negative momentum can be a black hole whose gravity is difficult to escape.

Technology

In the past, organizations could have strategies that did not depend on technology.  Now days, it is hard to imagine any strategy that did not depend on technology in at least in some fashion.  In some cases like tech companies or web companies, the technology is the strategy.  For most industries, technology merely supports or enables the strategy.  In any case, effective strategies will always involve some use of technology.

Choosing the Right Strategy

Of all the Critical strategies, the one with the highest payoff is choosing the right strategy.  While organizational devote some time to strategic planning, they may not necessarily devote the right time, people, and resources needed to determine a break-through strategy.

Very often, choosing traditional strategies (increasing product quality, reducing costs, driving revenue) are either Quagmire or Distraction strategies.  In contrast, the strategies chosen by creative leaders like Steve Jobs (integrate music hardware, software, and music distribution), have enormous payoff if they succeed.

Whatever strategy you choose, it should be one that seeks to develop sustainable competitive advantages throughout your organization and industry.  While it depends on your exact organization and industry, competitive advantage can include key technological advances or initiatives, world-class customer service, or expertise.  In addition, developing core competencies such as marketing and product management, process improvement, innovation, or sales can be distinct competitive advantages that propel your organization ahead of the competition.

Strategic Delegation – Important skill for creative leaders

After mastering the basics of “how to delegate”, an effective leader will quickly shift his or her focus to the next two questions – what projects do I delegate, and to whom?  If these questions are not asked and answered, the leader will continue to flounder doing too much routine work, micromanaging and delegating ineffectively.  This essay will help answer these two questions, with the help of this nifty chart I created featured below.

Routine Work – Newbies

In any setting, there are really only four categories of work to be done.  The majority of work is the “routine”, day-to-day work of the organization or department.  This type of work is generally not extremely difficult, nor is extremely mission critical, yet it has to get done.

Don’t assume, however, that routine work has to get done – frequently strategic actions involve the elimination of routine work through process improvement, technology, or other means.

Examples of routine work vary greatly according to the organization, but in a law department such as where I work, it might include customer contracts of relatively low value, or reviewing marketing materials or other documents.

Routine work is ideal for inexperienced, younger workers to handle.  If they make a mistake, it will generally not “burn down the building”, so to speak. And there is tons of it – plenty to go around.

And more importantly, it is precisely the type of work that you, as the leader, should not be doing!  If most of your day involves doing routine work, something is wrong.  If you keep doing routine work, you rob your staff of development opportunities and prevent yourself from tackling the important, strategic work you should be engaged in (like developing your staff) and other mission critical objectives.  Getting rid of routine work helps free up your mind, which, once it is de-cluttered, will often identify work that is, in fact, strategic in nature.

In addition, if you are delegating well, you will find that, very often, your staff can do certain routine work much better than you can.  This is one of the more pleasant surprises about delegating well – when your delegate turns in a stellar work product, far better than you could or would have done.

Difficult / Complex  – Niche Players

Some work is hard.  Not that it is so earth-shatteringly important, but it can be difficult, tricky, or complex, but it nonetheless, needs to get to done.  While I am a big fan of eliminating work through a zealous commitment to process improvement (I am very diligent if work has to be done, but unmotivated if I believe that the work could be streamlined or eliminated), there is a lot of work you just can’t get rid of, and thus, someone has to do it.

Work is difficult for many reasons, including that there is a high-dollar amount at risk (high-value contracts), it requires a specific skill set (as in an experienced contract attorney), or involves a number of moving parts.

Difficult work should be sent to “niche players.”  These are persons that have a specific skill set that is well-adapted to handle the particular work, including the right technical skills, knowledge, and experience.  Unfortunately these niche players often have certain limitations such as poor social skills, low motivation, or inadequate skill sets that keep them from developing into “stars”.

While niche players usually don’t reach star status because of their limitations (and therefore handle difficult and important work), they can indeed be trained to handle difficult or specialized work.  For example, a factory worker that could never design a car as an engineer may be capable of being trained to weld a very difficult joint on the assembly line in a highly competent fashion.

A key job of a leader is to train his or her new workers to handle increasingly difficult work.  This training can be “trial by fire” on the job, or could include additional educational training or mentoring.  It can also be achieved by specialization, giving one person on your team that certain type of work until they become experts at it.

Semi-Strategic – Rising Stars

Semi-strategic work is work that is important but not very difficult.  Just as work varies in difficulty, it is also varies in terms of its importance.  Important work could include tasks that help generate new products or services, bring in key clients, recruit key employees, streamline processes, or secure important resources.  Importance also depends on circumstances and timing; work that is unimportant at one point can be become very important at another time.

Work that is important helps organizations move forward is key areas and has a large downstream impact on the organization, such as increasing or conserving organizational resources, improving the composition of your team, or developing certain skills.

In contrast, work that is of little importance tends to have an impact that is either small or isolated.  In other words, doing unimportant work does not really change your organization’s position in any significant way.

Semi-strategic work is great for rising stars.  Rising stars are highly talented, responsible individuals that have great potential, but are currently inexperienced or lacking key competencies that they will eventually develop.  Handling important (but not overly difficult) work helps rising starts grow into stars.  In addition, their responsible, “can do” attitude ensures that the important work gets done in a timely fashion, and thus, moves the organization forward.

Strategic – Stars

The last category of work is both very difficult and very important.  Doing this work and doing it well has the potential to move the organization forward in very significant ways.  However, because the work is very difficult, if it is done poorly, it also has the potential to either hurt the organization significantly or lose much of its intended value.  As the leader, you should strive to work in the strategic quadrant as much as possible, including by developing your rising stars into stars, though some level of monitoring of the difficult work is often wise.

Examples of strategic work are hiring the right person for a key position, developing your future leaders and staff, or completing key organizational initiatives.  Other types of strategic work can include process improvement initiatives (which can eliminate costs and labor and thus increasing organizational resources) or innovative projects that can change a business’ balance sheet nearly overnight.

Strategic work is very often non-urgent work that is hard to complete because of limited resources and time constraints.  Thus, a constant challenge of leaders is to free up their resources from routine work so they can work on semi-strategic or strategic projects. Spending more time on strategic work tends to generate build yields that pay increasing (or even exponential) dividends over time.

Commonly Made Mistakes With Delegation

A common mistake of leaders is that they spend inordinate time on routine or difficult work that they should be delegating to newbies or niche players.  As a result, these leaders have little time to work on strategic or semi-strategic work.  In addition, their propensity towards micro-management means their staff is not growing, leading to unsatisfied workers and missed opportunities.

Another common mistake is that leaders do not take the strategic action of developing their staff.  This takes time, effort, patience, coaching, as well as funds for additional education and training.  Without efforts to develop staff, newbies do not grow into niche players and rising stars never reach star status. As a result, leaders have fewer qualified resources to assist them with strategic, semi-strategic, or difficult work.

A third common mistake is mis-judging the nature of the work.  Sometimes we under or over-estimate the difficult or importance of a project.  When this happens, we usually find that we have delegated the work to the wrong person, and then have to make course corrections – adding additional resources, providing support, or reassigning the work to the right person.

A fourth common mistake is misjudging their staff.  Sometimes leaders think someone might be up to a big challenge, while in reality they are not ready or willing.  Other times they might not have known about a certain trait or weakness of the person, which is revealed by unfortunate circumstances.  When this happens, leaders need to make sure they are still the right person to handle the assigned work, or they may need to conduct some quick damage control.

A final commonly made mistake when delegating is failing to retain responsibility for the delegated work and failing to hold the delegated person responsible.  Delegating work does not relieve you as the leader the responsibility for getting that work done.  While you don’t want to micromanage, you should retain oversight, especially for difficult, semi-strategic, or strategic work.  Likewise, you should hold responsible those to whom you have delegated the work for complete it successfully.

One way to ensure that you don’t make these mistakes is by progressively delegating more difficult and important work to your staff members.  Doing this gives them the chance to grow as well as you the opportunity to understand their strengths and weaknesses, which information you will use when making future decisions regarding delegating additional projects.  This helps you avoid delegating strategic work or giving someone a strategic role in an organization before they have proven themselves.  It is generally unwise to put the health of your organization at risk, though sometimes you should bet on a rising star that is progressing.

Author’s Note:

As a leader that is new to delegating, I am constantly making “little” learning mistakes as I delegated.  For instance, I thought one litigation matter was semi-strategic (and thus brought in a rising star to help), but it turned out it was strategic due to the sensitive nature of the litigation, and thus I should have kept the matter closer to home.

Other times, I have delegated the right task, but I have done so in the wrong way.  It is best to “prepare” people to receive assignments, making them in person or over the phone.  This is particularly true in the volunteer setting where I have limited authority as a leader.

One key to improve your delegation skills is to increase your “contextual” intelligence.  This helps you read people, work, and situations so you can determine to delegate what work, to whom, and how to delegate it.

Learning to delegate has changed my life in a huge way.  Rather than struggling endlessly with keeping my home clean and keeping up my large garden, I have found reasonably-priced “niche players” that do the work 5X faster and better than I could do.

This has left me with more time to do I what I do best, writing about delegation.  In addition, the congregation where I volunteer as an assistant leader has made huge steps forward over the last few months as we have learned the art of “strategic delegation” (with attendance increasing from a 52-week low of 22 to 52-week high of 49 in just two and half months during the summer).