By: Kyle Robertson on July 29th, 2025
5 Executive Hiring Problems Solved by Retained Search
Executive hiring is the most important recruitment decision your organization will ever make.
A great executive hire can transform your company, allowing you to identify and execute bold new strategies. Hire the wrong person, however, and it could have catastrophic consequences.
Many organizations spend a long time on high-level hiring decisions, with average recruitment cycle times of around 6-9 months. Despite this, the failure rate is high, with around 40% of executive hires failing to reach expectations within the first 18 months.
The truth is, executive hiring is completely different from regular staffing. It can present a whole range of new problems, each of which requires a new solution.
Hiring executives through retained search
First, let’s discuss the retained search approach to executive hiring.
Hiring an executive is more complex than simply placing a job ad and sifting through the pile of candidate applicants. Recruitment agencies generally aren’t much help in this scenario. Instead, you’ll need to work with a specialized executive search firm.
What does this mean? The main features of retained search are:
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Retained search is focused on outcomes. The retainer ends when the best possible candidate has joined the C-Suite. Achieving this will require a retained search consultant who knows how to overcome the biggest challenges of executive recruitment
5 biggest problems in executive recruitment
While many organizations attempt to handle executive searches internally or through traditional recruitment methods, the complexity and unique demands of filling executive roles and senior leadership hiring often require a more sophisticated approach. Here are the five biggest problems plaguing executive recruitment today, and how retained search partnerships can provide the solution.
1. Defining candidate requirements
Executive hiring goes beyond simply looking for candidates with the right experience and qualifications. The leadership team will need to have in-depth discussions that go to the heart of your mission. What is your culture? How do you live your values? What role will the new executive play in your company’s evolution?
These are high-level conversations, and not all stakeholders have an equal voice in the discussion. As a result, companies can fail to form a clear picture of their ideal candidate. This leads to longer hiring cycles and, ultimately, poor outcomes.
How retained search helps: Retained search consultants begin their mission by learning as much as possible about the organization, including its culture and strategy. They will then speak to stakeholders and learn more about what’s needed from the new executive, whether that's the CEO, CFO, COO or other C-level position.
By following this approach, you’ll begin the executive hiring process with a well-defined candidate profile. This improves the chances of finding and hiring the right person for the job.
2. Building a recruitment strategy
Finding suitable candidates is often the biggest challenge in executive recruitment. Around 47% of companies say they’ve struggled to find top talent, and this problem is worse for organizations with limited resources.
Part of the problem is that many executives are not active job seekers. Finding talent often means building a passive recruitment strategy, which can take substantial time and effort. It also involves finding ways to access new talent pools and reach out to potential candidates. Without these talent sourcing strategies, companies often find that they simply can’t reach the right people.
How retained search helps: Working with an external recruiter is a great way to expand your talent sourcing ability. The right consultant will have their ear to the ground and know candidates who are waiting to hear about new opportunities.
Retained search consultants also have their own toolkit for finding executive talent. This can include specialist talent sourcing software, access to professional groups, and an extensive network that can be used for referrals.
3. Creating attractive compensation offers
Executive compensation isn’t as clear-cut as employee remuneration. Often, there is a greater range of payment options on offer, including stock options and bonuses related to strategic targets. Also, the compensation will vary depending on the expectations and responsibilities awaiting the newly hired executive.
Compensation is also a vital tool for attracting suitable talent, especially when passively recruiting. The core package needs to be enticing to the most appropriate candidates, while also being sustainable for the employer. Striking this balance can be incredibly difficult.
How retained search helps: Retained search consultants have access to extensive salary benchmarking data. Such data can help inform a compensation offer that will meet expectations for people who match the ideal candidate profile.
Executive recruiters also have a lot of experience dealing with candidate negotiations. They’ll know how to present the compensation offer in a way that appeals to talent, whether that means highlighting salary or focusing on other benefits.
4. Managing communications
Many executive searches require absolute confidentiality, whether due to succession planning, competitive sensitivity, or the need to avoid disrupting current team dynamics. Internal recruitment efforts often lack the infrastructure and expertise to maintain the level of discretion that sensitive executive searches require.
There are also the logistical challenges of scheduling, communication, and setting expectations between candidates and the hiring panel. Both parties tend to have limited availability, which makes it hard to arrange interviews and meetings. Without a solid communication strategy, the desired candidate might become disengaged and leave the process.
How retained search helps: Professional search firms are built around confidentiality protocols. They serve as neutral intermediaries, protecting both the client organization and potential candidates throughout the process. Their reputation depends on discretion, making them trusted partners for sensitive placements.
Retained search consultants are also in a perfect position to manage communication and scheduling tasks. They can help structure the hiring process in the most time-efficient manner, plus they can take responsibility for keeping the candidates engaged during the search process.
5. Maintaining objectivity
Culture fit is an essential part of hiring, especially when recruiting senior executives. However, culture can be subjective. Senior leaders might have a C-Suite perspective of the organizational culture, and this might bias them toward candidates that fit their views, rather than the requirements of the role.
In some cases, this can lead to blind spots and bias, which will skew the hiring process and possibly lead to diversity and equity issues. Conflict is another possible issue, as senior stakeholders might disagree about the best way forward. Both of these problems are common when the executive hiring process lacks an objective voice that can offer impartial suggestions.
How retained search helps: Experienced search consultants are skilled at assessing cultural fit through behavioral interviewing, reference checking, and deep organizational analysis. They understand how to evaluate not just what candidates have done, but how they'll perform within specific organizational cultures and team dynamics.
Retained search consultants can also provide an objective, third-party perspective on culture fit and candidate suitability. This helps avoid any unconscious bias in the hiring process, ensuring that you always pick the right person for the job.
Getting executive hiring right
Retained search partnerships offer more than just candidate sourcing. They provide strategic guidance, objective assessment, confidential handling, and the experience needed to navigate the unique challenges of executive-level recruitment. From defining your ideal candidate profile to negotiating complex compensation packages, a skilled search consultant becomes an extension of your leadership team.
The question isn't whether you can afford to invest in professional executive search services—it's whether you can afford not to. Open positions represent lost opportunities, strategic delays, and potential competitive disadvantage.
At Helios HR, our executive search expertise helps organizations identify and secure the leadership talent that drives transformation. Our comprehensive approach includes:
- Retained & Executive Search - Dedicated partnerships focused on finding your ideal executive candidates
- Strategic Leadership Assessment - Deep evaluation of candidates' cultural fit and strategic capabilities
- Compensation Benchmarking - Market-informed guidance on competitive executive packages
