Woman planning mentoring program

Manual Mentoring Challenges & Pain Points

There’s a reason 71% of Fortune 500 companies offer mentoring programs to their employees. A well run mentoring program is an effective strategy to engage, develop and retain more people at an organization.

But the key phrase there is well run, because if a program isn’t, it can actually do more harm than good. According to The Atlantic, “researchers have established that negative mentoring experiences caused more intense emotional and behavioral responses among employees compared to positive incidents.” So when it comes to mentoring, it’s not just the thought that counts – it’s the execution. In light of this, the question of whether or not to use mentoring software is an important one.

person working on a tablet

Not every mentoring program needs software, but as your program grows and its needs evolve, you’ll likely encounter some mentoring challenges that software can soothe. Whether you’re bottlenecked by repetitive program maintenance, struggling to formalize your program, or trying to prove your program’s impact with data and reporting, it might be time to let software pick up some of the heavy lifting.

Software can remedy your current mentoring challenges, fortify your program with meaningful data, and future-proof your program to allow for continuous growth.

So what are the signs it’s time to make the jump to mentoring software?

Related: Online Mentoring: How Technology Can Enhance Mentoring Connections

man and woman outside with computer at table talking about manual mentoring challenges

Six Mentoring Challenges of Manual Programs

We’ve helped hundreds of organizations navigate the decision to invest in mentoring software. Since every mentoring program is unique, there’s no one-size-fits-all advice for this decision. Rather, it’s best to audit your program to identify your current pain points and inefficiencies, while mapping out your program’s trajectory and future needs.

Here are the most common pain points that drove our customers to software:

Inability to Scale Your Mentoring Program

Program growth has a direct impact on the time and effort it takes the manage each moving part within your program. Each additional person is one person you need to spend time matching, guiding, and following up with. In short, program growth will exaggerate any other pain points and bottlenecks you have.

So what’s the magic number? While every mentoring program is different, we’ve found that once a program has around 50 participants, the increased workload starts to bottleneck program administrators. You’ll know it’s time when you start to feel overwhelmed.

With software, recurring tasks can be automated with speed and precision, making it easy to scale up without adding extra work. One of our own customers, the Society of Petroleum Engineers grew its program by 33 percent after adopting Chronus software.

Inability to Quickly Make the Best Matches

When you’re matching 20 mentees with 20 mentors, finding the best match might be fairly straight forward. But what happens when that number doubles, or triples? At a certain point, matching manually becomes unmanageable. That is, unless you have unlimited time, coffee, and a sharp eye for nuance within your participants’ needs and skillsets.

Software helps you streamline this process in a couple of ways. Most software solutions will use an algorithm that automatically suggests the best match by analyzing the data in each participant’s profile. The right solution will allow you to match based on the factors most important to your program, such as location, department, seniority, gender, ethnicity, etc.

A sophisticated solution will let you choose from admin match, self match, bulk match, or a hybrid style. As the name suggests, admin match gives administrators the final say, while self match gives mentees the power to match themselves. Large programs can use bulk match to match hundreds of participants simultaneously, which can save a ton of time.

Our own MatchIQ® algorithm offers flexibility and precision to help organizations match participants based on their program goals.

Inability to Guide & Track Mentoring Program Progress

Mentoring is a highly personalized mechanism for development. Each relationship is guided by the participant’s unique goals. This is great for participants, but not so great for the person trying to make sure everyone’s on track. With a manual program, maintaining real-time data on progression is impossible, which makes it hard to intervene when something’s gone wrong.

Providing guidance and structure for participants is often overlooked. As The Atlantic explains, “…much of the problem with corporate mentorship programs is that they miss an opportunity to create a formal, structured path for mentors and mentees.”

Software gives you the tools you need to provide structure while still allowing for customization. Each pair will be working toward different goals, but with software you can setup flexible workflows that guide each pair along regardless of the specifics and automatically track and report on progress.

Inability to Measure Program Impact

With the right software, you’ll have dozens of robust reports that highlight various indicators of program and connection health. All of that data means you can quickly track and analyze the performance of your program. To prove mentoring ROI, you can then connect your mentoring outcomes to business outcomes such as:

  • promotion rates
  • engagement
  • retention

Properly measuring your program gives you the support to showcase mentoring’s impact on your organization to stakeholders and leadership. It’s imperative to connect mentoring activities to your employee outcomes to prove mentoring is valuable to your company. And not just valuable, but imperative.

Inability to Gather Mentoring Program Feedback

Participant feedback is crucial to fine tuning your program and measuring success. With a small group, it can be easier to get a consensus on what’s working and what’s not, but feedback will likely be more anecdotal, less data driven, with less documentation. With a larger group it’s simply going to be harder to get an objective feel for what the masses want. Not to mention the time you’d spend reaching out to participants and following up if they don’t respond.

Software can enable you to have a more agile mentoring program by automatically surveying participants at predefined intervals. Results are then conveyed in a way that’s easy to digest visually. This lets you see early on if participants are satisfied with the program and if there’s anything you can do to improve the program. Being able to correct course as you learn your participants’ preferences means you can efficiently optimize your programs to get the results you want.

Inability to Automate Mentoring Program Communications

For optimum mentoring program health, it’s important to check in with participants to make sure they’re happy with their match and their mentorships are productive and meeting expectations. With a small group, you may be able to manually keep a pulse on your program with some emails, phone calls and impromptu hallway conversations. But without the infrastructure to support and document automated communications, status updates will likely be unstructured and poorly tracked. And the larger your program grows, the more cats you’ll need to herd.

One of the perks of software is the automation of communications. Whether you’re doing QA on the match or nudging participants along with reminders, software lets you automate targeted email campaigns, giving you the precision of only sending emails to those who haven’t completed a specific task. With software, targeted communications are a breeze, and the software itself serves as a central communication hub, which lessens the chance that you or your participants will lose track of conversations.


Additional Benefits of Workplace Mentoring Programs

Mentoring programs in the workplace can help the success of a business that has to keep up with constant changes. A structured mentoring software program can respond to employee needs and enable their motivations. Other benefits of mentorship in the workplace include:

Creating a Learning Culture

Implementing a mentoring program fuels a company culture that values the importance of learning and development. Employees can visualize their future and take steps to reach their goals when they are paired with a mentor who can guide their career development. Encouraging employees to gain knowledge from their peers and senior leaders promotes a collaborative learning environment.

Promoting Personal and Professional Development

Mentors listen to and guide employees, creating a safe and comfortable place for learning. Making mistakes and taking risks are all part of the journey of career development. Employees that are constantly learning promotes a culture of innovation.

Reducing Scrap Learning

Mentoring is a continuous method of learning from others that provides a direct plan for reinforcement and on-the-job application. As companies battle scrap learning—the learning and training that is very applied back to the business, mentoring can be a vital asset in reducing costs of learning and training efforts that aren’t serving the organization or employees long-term. Mentoring supplements learning programs to better support employees in retaining the knowledge and skills needed to meet objectives, leading to greater impact for the company.

Improving Mental Health and Wellbeing

Some employees are hesitant to go to their manager when they have an issue at work. Their peers may not always be able to help if they have never faced a similar issue. Mentoring programs provide employees with someone to turn to for guidance in tackling a responsibility, dealing with a sensitive workplace situation or navigating the road to that next stretch assignment or promotion.

A mentor/mentee relationship can also provide emotional support during troubled times, whether this is when a difficult situation with a manager arises, an organizational change takes place or when health and family matters create discord. Having someone to turn to in a crisis leads to less stress and anxiety for employees, as they navigate a difficult time.

Increasing Job Satisfaction and Reducing Turnover

A mentoring software program can build a positive work environment. These supportive connections can build an empathetic workplace culture of belonging. This can increase job satisfaction which in turn can reduce the number of turnovers and more.

two men sit at table discussing mentoring challenges


You’ve identified your current mentoring challenges, but now it’s time to look into your crystal ball and think about how your program will grow in the future. Some of your future needs may include capabilities listed in the previous section, but it’s important to also make sure the software you choose will grow with your program.

Running your mentoring program manually may be doable with a small program, but if you find yourself becoming frustrated with the day-to-day work of program maintenance, it might be time to upgrade. You’ll save time, your program can scale to impact more people, and you’ll have access to data that can help you show business results and ROI.

With software doing the time-consuming, repetitive work for you, you’ll be free to focus on more strategic aspects of the program and your other responsibilities.

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