Employees’ Long-Term Interests Matter

Invest in thoughtful mentorship structures from the start

Mentorship and coaching are critical aspects of a company’s operations. When executed properly, they have the potential to earn a new hire’s loyalty by effectively building them up to be an employee capable of meaningful contributions. Ongoing and thoughtful opportunities can then help retain that employee over the long run, giving them the opportunity to pay their institutional knowledge forward by building up the next generation.

In spite of these benefits, mentorship and coaching structures at growing tech companies are often poorly organized. The evidence of this can be seen right away during the onboarding process, and is further on display by the average employee’s unnecessarily shortened tenure. Having done the difficult work of recruiting valuable talent, a company should have structures in place which encourage growth and retention.

Incentive veteran employees to help with onboarding; make them feel valued and valuable for helping new hires catch on

Before describing how mentorship and coaching should work, it’s important to outline the insufficient ways in which they too often operate. A new employee’s first day is usually filled with the standard, easily organized HR onboarding. Evergreen knowledge, such as company benefits and sexual harassment policies, is communicated in a neutral conference room. Once completed, the new employee is escorted to their corner of the company and given a proper introduction to their new team. Of particular note is someone who has been taped by management to be the new employee’s mentor. Strictly speaking, this person may not have volunteered for the job. A better word for it would be “volutold”; they were informed that it would be in their best interest to shoulder this responsibility.

It doesn’t take long for the relationship between this mentor and their new mentee to devolve into something that leaves both parties frustrated. From the outset, their dynamic is ill-defined and governed by few parameters. They may not have structured sessions together; instead, the mentee may simply sit next to their new mentor, bugging them each time a confusing juncture is reached. Their relationship may not have an agreed upon expiration date, a particularly stressful prospect for the mentor, given their own, independent and considerable workload. Making it all even more frustrating is the fact that the mentor’s effort to bring their mentee up to speed is largely invisible to the rest of the organization. It is taken for granted and never appreciated by anyone other than the mentee, making the whole thing feel like a burdensome chore that is a distraction from the workflow they were actually hired to execute.

Clear Expectations Enable Success

Communicate clear parameters and obligations amongst mentors/mentees

This initial experience is just one specific form of mentorship; there are many other opportunities that extend throughout an employee’s time at a company. I’ll consider those in a bit, but before that, it’s worth stressing that the just outlined scenario underscores a few fundamental points. There are a handful of common errors that make productive mentorship processes difficult. Mentors being “voluntold” is one of the original sins, especially when it’s followed with a lack of resources or appreciation from the company at large. The absence of a thoughtful and well communicated structure to the mentor-mentee relationship also strains things, leading to perhaps the biggest problem of all: mentors often failing to patiently and effectively guide their mentees. This is important work, and should be treated accordingly. 

The antidote to bad mentorship is simple. Simple, though, is no synonym for easy. A company needs to draw up thoughtful processes characterized by clearly set expectations. Mentees need to be informed on how best and under what specific circumstances they can seek out their mentors. For their part, mentors need to be given recognition for the vital service they’re providing, which includes making this relationship an official part of their responsibilities rather than one more log tossed carelessly on an already borderline inferno of workflow.

The Five Types of Mentorship

A careful study of a fully Tech Enabled company reveals five types of mentorship. Each of these is its own unique tool, meant for use in specific circumstances They are:

  1. Buddy 
  2. Office Hours 
  3. Coaching 
  4. Mentorship 
  5. Forum


It’s worth taking a moment to break each of these types down in order to examine both their individual parts and how they connect and feed into one another.


Create standard, thoughtful onboarding processes that new hires can easily navigate

The previously detailed hypothetical of a new hire’s first days following their conference room date with HR is an example of poor Buddy mentorship. A common mistake when creating this relationship between employees is to reinvent the wheel each time, assuming that every new hire requires an individualized experience. With the proper structure throughout the organization, however, this shouldn’t be the case. Ideally, the buddy (or mentor), isn’t just answering questions. Instead, they are helping to guide their mentee by further contextualizing easily accessible processes, now and again guiding them along a path designed by management. The more thoughtful the onboarding, the less necessary it is to chew up the clock with energy consuming question and answer sessions.

That isn’t to say that, even under the best circumstances, it will never be necessary for a buddy to set aside time for a straight Q & A. When this comes to pass, however, both parties will benefit from agreeing on specific parameters for how to set this time aside. Maybe that looks like a buddy telling their mentor that they are free to answer any question on any day, but only between 11 AM and 1 PM. Maybe it’s a buddy making themselves available all day Tuesday and Thursday, but never on Monday, Wednesday and Friday. Or maybe it’s any day and time, but with the explicit agreement that the mentee will only reach out for help if they’ve been struggling with an issue on their own for over an hour. 

Encourage new hires to troubleshoot on their own before turning to the help of a mentor

The specifics of the arrangement are less important than the fact that all sides know what to expect and can plan accordingly. It’s in no one’s interest to have a new hire spinning their wheels needlessly. That said, fostering a sense of autonomy is critical, and the ultimate goal is always to improve the mentee’s time-to-competency and their sense of belonging. The buddy should serve as a designated go-to-person that helps them get unstuck, but only after they have tried valiantly to unstick themselves. As the time between check-ins lengthens, less and less will be demanded of the buddy until, finally, at a predetermined date (say 6 months from initiation), the relationship will reach a predetermined end, and the two employees will transition into regular colleagues.  

There is clear evidence of a successful buddy mentorship. The new hire should feel like they always have someone to talk to, of course, but that they also always know how and when to talk to them. As a result, the new hire doesn’t hesitate to be vulnerable with their buddy, in part because they haven’t been made to feel like a constant pest. Instead of immediately pulling on sleeves and asking a barrage of questions, they were given a thorough and competent onboarding playbook that only needed a few specific holes filled.

Celebrate productive buddy’s; use their success to communicate company values

On the other side of the equation, the buddy isn’t tapped at the last moment and forced into the role. They are instead prepared for the responsibility, ideally seeing it as an opportunity to pay forward their institutional knowledge and strengthen their team specifically and the company generally. Thanks to their preparation, they are able to sit down immediately with their mentee and set reasonable expectations, making clear what they can and can not assist with. They would create a deliberate and specifically delineated relationship that would insure the integrity of their workflow. In the wake of a successful mentorship, the buddy would be publicly recognized for their important contribution, which would send a strong internal signal regarding the organization's values.

Success at this stage means success at the first stage. A new hire feels confident in their decision to take this job. A veteran gets to shine by performing acting generously. And management earns the loyalty of both parties, increasing the odds of long term retention and deepening organizational culture.

Office Hours

Create ongoing opportunities for formal mentorship by making SMEs easily accessible 

At a certain point, a new hire transforms into, well, someone who is no longer so new. Fueled by a few productive months in which they were gently guided by a capable buddy, the former mentee finds themselves humming along, shipping code and adding value. Soon, though, they encounter a novel situation that trips them up. This is no longer a question of onboarding; the help needed is specific and less intrusive and will only last a short while. 

In this scenario, the employee should be able to easily locate a relevant subject matter expert and “sign up” for a slice of that expert’s time and assistance. Part of what sets Office Hours apart from a Buddy is that, in this situation, the mentor and the mentee could be peers. They may not be separated by any sort of formal or even informal hierarchy. It’s as simple as one of the pair needing help to quickly acquire a new understanding, and the other being perfectly suited for the task. 

Monitor these relationships; use them as a means of identifying where employees are getting stuck

This relationship doesn’t last long and doesn’t even need the formal structures which govern the Buddy system; the pair can meet any time the mentee feels stuck, and for as often and long as it takes for them to get unstuck. The pair can convene in whatever format feels most natural, be it in person or virtually. Both parties should know in advance how their meetings will go and what will be covered.

Management makes room for and facilitates these sorts of arrangements because a human touch remains necessary long after onboarding has served its purpose. In doing so, the company’s best interests are also being served. There is no disruption to a steady, productive output, while those “hosting” office hours are able to gain valuable insight and report back on what sharp edges may be hiding in the company’s software, services or processes. Ideally, management will use this feedback to further improve things, making Office Hours less necessary as the company reaches the latter stages of Tech Enablement.


Make coaches available to employees who are stretching themselves in new ways

Coaching comes still later in an employee’s work life cycle, when they are breaking off a large, difficult project, often for the first time. The assistance needed is more complex than anything that will fit into the Office Hours format, and so a suitable mentor needs to be a specific subject-matter-expert. In this case, the mentor may very well be above the mentee on the company or team org chart. This relationship follows an apprenticeship model, wherein a senior employee helps someone more junior increase their expertise step by step.

Obvious though it may seem, it’s worth stating that the goal of Coaching is to increase the likelihood of a mentee succeeding at a new, even risky project that stretches their skillset and experience. The mentor should shepherd the mentee through the early stages of the project kick-off, thereafter providing ongoing weekly support and when-necessary course corrections that last for the duration of the project.  The ideal outcome of Coaching is for the mentee to deliver on their goals, demonstrating an ability to run a project end-to-end, in the process potentially making a case for themselves as someone who should be considered for a more senior role at the company.

Publicize this success to prove to your workforce that they can successfully grow in house

From the company’s perspective, successful Coaching is a godsend, working as a form of vertical development that increases the capability of its workforce.  This will keep home-grown talent in house, as employees are given both the opportunity and capability to grow. It demonstrates that staff need not look elsewhere for exciting opportunities that lead to new forms of success. In the process the company retains institutional knowledge while creating the next generation of mentors.


Encourage employees to strategically plot their career growth with senior employees who can offer unbiased advice

While I’ve been using the terms “mentor” and “mentee” in each of the previous scenarios, the term Mentorship means something a bit more specific at a Tech Enabled company. Mentorship is distinct from manager support, and isn’t tied to any specific project or skill development. It is instead centered on the mentee’s long-term career growth. 

Mentees should be able to seek out and connect with more senior veterans at their company who have walked a similar path and don’t possess any sort of conflict of interest. When the mentee finds themselves at a difficult juncture, feeling unsure as to how they might move their career forward, they can find a resolution with the unbiased advice and support of a mentor. The pair could meet once a week or once a month; most important is that the mentee drives the conversation, conveying their hopes and, if need be, doubts. The mentor is there to listen, reflect and share from experience. They are also there to hold the mentee accountable, which may come in the form of a shared doc used to capture, evaluate and grade a mentee’s goals.

When a company makes room for this sort of relationship, it demonstrates that it cares about its workforce and not simply productivity. Mentorship programs can be difficult to launch; they often feel like online dating, with people nervous and unsure how to break the ice. When run at scale, though, they can improve company culture and aid significantly in workforce retention.


Utilize forum groups when mentors are otherwise in short supply; champion them as a legitimate use of work hours

The final form of mentorship occurs when groups of peers get together in order to exchange knowledge as equals. This phenomenon often happens organically, meaning an organization should have little difficulty corralling it and making it a formal part of operations. Forums consist of experiential learning in small groups bound together by common interests. The ideal size is roughly five to ten employees. There are no mentor-mentee or customer-vendor dynamics in these relationships, which makes them ideal for companies that suffer from a small pool of formal mentors. 

The point of a Forum is for employees to learn from the experience of their peers in a trusting and safe environment, discussing their personal and professional highlights and lowlights. These groups can meet at any time, though employees should be past the onboarding stage before joining, the better to have something to bring to the table and contribute. Groups will ideally meet for roughly once a month over a period of 6 months once before they are shuffled and rotated in new arrangements.

We All Need to Acknowledge the New Work Recipe

Recognize various forms of mentorship as a critical means of creating social connections

An ongoing challenge of the post-Covid work era is the erosion of employee loyalty now that many of us don’t share a common workspace and, by extension, daily work culture. We are more alienated than ever as a result of our no longer getting lunch together or running into one another at the coffee pot. Mentorship represents an opportunity for people to meet and get out of their bubbles. It allows employees to quickly feel like they are part of a supportive and positive environment, one invested in their catching on and contributing to the team and company at large, resulting in vastly expanded skill sets and satisfying career arcs.

Mentorship’s role isn’t simply to help navigate social, cultural or technical challenges, however. It also provides a social network, giving people the opportunity to plug into a community and understand an organization from multiple points of view. In so doing, mentorship boosts both morale and productivity in the short term, and retention in the medium and long terms. This is because mentorship demonstrates that a company is genuinely invested in the success of its employees, and that veteran employees are willing to go out of their way and even fight for the advancement of those more junior. 

Celebrate successful examples of mentorship at every stage of career development

Like so much of Tech Enablement, the best part of it all is that, when executed correctly, mentorship creates a virtuous cycle. In such an environment, a new employee is hired and moves efficiently through the onboarding process thanks to the help of a supportive and prepared Buddy who has set helpful and specific parameters to their relationship. Handed their first significant task some months later, that same employee clears what major hurdles they face thanks to Office Hours and the ability to easily seek specific guidance. Some more time passes, and this person is now given an even larger project, one that will make or break their desired ascension into a more senior role at the company. Coaching helps them deliver on the big issue and add new value to the company. At this point, they’re ready and qualified for a range of more serious promotions, and a Mentorship helps them to identify what they want and where they want to go. Simultaneously, they themselves sign up to be mentors in some capacity, paying it all forward and completing the circle.