Every year around this time, companies begin looking ahead. Budgets are taking shape, growth plans are being discussed, project pipelines are being evaluated, and leadership teams are deciding where additional people may be needed. Naturally, much of the hiring conversation centers on anticipated openings. If the company plans to enter a new market, increase production, expand a division, or take on additional projects, leadership begins estimating the people required to support those plans.
That is an important part of workforce planning, but it only addresses the positions a company expects to fill. There is another side of the organization chart that deserves just as much attention: the positions that are already occupied.
As companies prepare for 2027, I think there is value in asking a different question. Instead of looking only at who you expect to hire next year, consider which people and positions would be most difficult to replace if circumstances unexpectedly changed. That conversation can expose potential leadership gaps, development needs, succession opportunities, and recruiting challenges long before they become urgent.
The Position That Isn’t Open Yet
Most organizations can plan reasonably well for growth they can see coming. If there is a new division on the horizon or a larger project pipeline developing, companies can begin thinking about the operations, construction, land, finance, sales, or executive talent needed to support it. The more difficult situation is the vacancy nobody planned for.
A Division President may accept another opportunity. A long-tenured construction executive may decide to retire. A land professional may be approached by a competitor. An operations leader may relocate for personal reasons. None of those situations necessarily reflects a problem within the company. Good people make career and life decisions every day. What matters is how prepared the organization is when one of those decisions affects a critical position.
The impact can extend far beyond the responsibilities written in a job description. Experienced leaders often carry years of institutional knowledge, industry relationships, market familiarity, and an understanding of how decisions are made within the organization. In real estate development and construction, that knowledge can be especially valuable because so much of the business depends on relationships, market experience, judgment, and the ability to navigate complex projects and changing conditions.
The question, then, is not simply whether the company could fill the position. Almost every position can eventually be filled. The better question is what would happen to the business during the time it takes to find the right person and get that person fully effective in the role.
How Deep Is Your Bench?
Succession planning becomes more useful when companies move beyond identifying someone who could potentially assume a larger role and begin evaluating whether that person would actually be ready to do it. Ideally, organizations are developing people internally who can take on greater responsibility over time, but naming a potential successor is very different from knowing someone could step into the position tomorrow.
A company may have an excellent Vice President who could eventually become a President, or a strong Director who has the potential to lead a larger function. That is valuable. It may also be true that the person needs exposure to areas of the business they have not yet managed, more experience leading larger teams, or additional time working directly with customers, partners, investors, or other stakeholders. Succession planning works best when those gaps are recognized early enough to do something about them.
The same thinking should extend beyond the executive suite. One of the hardest people to replace may be a senior land professional with decades of local relationships, an operations leader who understands how several divisions work together, or a construction executive who has learned through experience how to identify problems before they become expensive ones. Sometimes the greatest talent risk in an organization is attached to a title leadership would never think to include in a formal succession plan.
Looking at the organization this way changes the conversation. Rather than asking only who is next in line, leadership can start thinking about where knowledge sits, where relationships sit, and where critical capabilities are concentrated too heavily with one person.
Don’t Just Plan Headcount. Plan Capability.
Workforce planning often becomes a numbers exercise. Companies determine how many people they employ today, estimate how many they will need next year, identify anticipated openings, and build a hiring budget around the difference. That process is necessary, but headcount alone cannot tell leadership whether the organization has the capabilities required for where the business is going.
Two people with the same title can bring very different experience to an organization. An executive who has spent years opening new markets may offer something entirely different from a leader whose strength is improving the performance of an established operation. A construction executive who has led through difficult market cycles brings a different perspective from someone whose career has primarily developed during periods of expansion. Neither background is inherently better. What matters is whether the experience matches what the business will need next.
This distinction becomes particularly important when companies are planning several years ahead. Growth may require capabilities that are not immediately obvious from an organizational chart. Entering a new geographic market, changing product types, expanding a development platform, increasing operational complexity, or preparing the next generation of leadership can all change the type of experience a company needs.
The most useful workforce plans therefore connect talent directly to the business strategy. Instead of simply asking how many people will be needed, leadership can ask what the organization needs to become better at and whether those capabilities already exist inside the company.
Five Questions Worth Asking Before 2027
A simple exercise can help reveal some of these less obvious talent needs. Before finalizing next year’s workforce plan, leadership teams can look at the organization from both a growth and continuity perspective and ask:
Which positions would create the greatest disruption if they unexpectedly became vacant?
Where do we have a promising internal successor who still needs additional development or experience?
Which people hold important market relationships, technical expertise, or institutional knowledge that is not widely shared across the organization?
What capabilities will our business need over the next few years that are currently limited or missing?
Which positions would require a particularly specialized or difficult external search if we had to replace someone quickly?
The point of this exercise is not to predict turnover or assume someone is going to leave. It is to identify where the organization has depth and where it may be more vulnerable than leadership realized. Once companies understand those areas, they have more options. Some gaps can be addressed through development, mentoring, cross-training, expanded responsibilities, or a clearer succession path. Others may eventually require external recruiting. Either way, identifying them early creates choices that generally disappear once an opening becomes urgent.
The Talent Market Doesn’t Start When Your Search Does
There is another reason to think about critical roles before they become vacancies. The external talent market is already moving, regardless of whether your organization currently has an opening.
Experienced real estate development and construction professionals do not suddenly become candidates when another company needs them. Many of the people an organization would most want to hire are already employed and may not be actively looking at all. When they do consider an opportunity, they are evaluating more than a title and compensation package. Recent Recruiters Report coverage has explored how senior construction and development candidates increasingly approach opportunities as a two-way evaluation, looking closely at the organization, its leadership, stability, growth plans, and what the future might hold before deciding whether a move makes sense. What Top Construction Leaders Want Before They Say Yes
For employers, that makes preparation particularly important. When leadership has already considered what a critical role should accomplish over the next several years, what experience would be required, and how that individual would fit into the larger business strategy, an eventual search can begin from a much stronger position.
The opposite is also true. When those conversations do not begin until someone gives notice, an organization may be forced to define the future of the position while simultaneously trying to fill it. Those are two important decisions, and neither benefits from unnecessary urgency.
Internal Development and External Recruiting Are Not Opposites
There can sometimes be a tendency to view succession planning and external recruiting as competing strategies. If a company is committed to developing its people, the assumption is that leadership positions should be filled internally. If the company conducts an external search, internal development somehow failed.
In practice, strong workforce planning should create room for both.
Some of the best leadership transitions happen when organizations have deliberately prepared someone internally for greater responsibility. Internal candidates understand the business, relationships, culture, and history in ways an outside hire cannot immediately replicate. Developing those people also gives companies an opportunity to preserve knowledge and create visible career paths.
At the same time, there are moments when outside experience is precisely what the organization needs. A company entering a new market, changing strategy, expanding into another sector, or reaching a new stage of growth may need capabilities that have not yet been developed internally. In those situations, an external hire can complement the leadership already in place rather than replace the company's commitment to internal development.
The goal should not be to decide today whether every future role will be filled internally or externally. It is to understand which options are realistically available so that leadership is not making that decision for the first time after a critical position becomes vacant.
Before You Finalize 2027, Look at the Organization Differently
As 2027 planning takes shape, there will be plenty of conversations about new positions, budgets, projects, markets, and growth. Those conversations should absolutely happen. But before the hiring plan is considered complete, it is worth taking one more look at the organization chart.
This time, instead of concentrating on the empty seats, look carefully at the occupied ones.
Consider which positions the business depends on most heavily, where succession depth already exists, where promising people need more development, and where too much knowledge or responsibility may be concentrated with one individual. Then think about what the organization is trying to accomplish over the next several years and whether the capabilities required to get there are being developed today.
The goal is not to create a replacement plan for every employee. It is to understand where people and business strategy intersect so that important talent decisions can be made thoughtfully rather than reactively.
There will always be hiring needs that companies cannot anticipate. People retire, careers change, businesses evolve, and opportunities arise that nobody saw coming. That is part of running an organization.
But an unexpected vacancy does not have to create an unexpected talent strategy.
Sometimes the most valuable hiring conversation a leadership team can have is about a position that is not open at all.
Before you put away that organization chart, consider whether there are one or two positions that deserve a deeper conversation. Whether you are developing an internal successor, planning for future growth, or realizing that the right external talent may eventually be needed, thinking ahead gives you more choices. Fill out the form below to start a conversation with our team about the leadership and talent needs on your horizon.
