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9 powerful ways legal, finance, and HR can use AI

When you think of AI at work, it’s easy to picture marketers drafting blog posts or crafting social media content. But AI’s possibilities go beyond marketing. In fact, some of the most revolutionary uses of AI are happening in traditionally less front-facing roles such as legal, finance, and HR.

These departments are the backbone of any organization, handling complex tasks that require precision, analysis, and judgment. AI’s capabilities in these areas can save countless hours, minimize errors, and help teams make decisions more efficiently.

Let’s explore nine ways in which legal, finance, and HR departments can take advantage of the power of AI to transform their workflows.

Legal: AI tools for efficiency and precision

Streamline contract summaries

Contracts are often long, dense, and packed with legal jargon, but AI can simplify this process. Tools powered by AI can summarize contracts into plain English, highlight unusual clauses, and flag high-risk terms. Want to compare contract versions? Ask an AI tool to identify key changes, saving paralegals and attorneys hours of tedious work.

Example prompt:

“Compare these two versions of the vendor agreement and highlight differences in termination clauses.”

Draft policies 

Writing legal policies, such as Acceptable Use Policies or Non-Disclosure Agreements, is time-consuming. AI can take your specific requirements and generate a solid first draft, which you can refine for tone and compliance.

Example prompt:

“Write a GDPR-compliant NDA in a friendly but professional tone.”

Translate legal documents

Whether expanding globally or dealing with international clients, language barriers can be an issue. AI-enabled language tools can translate policies and contracts efficiently, saving you days of waiting on manual translations.

Finance: AI simplifying reports and forecasting

Automate monthly reports

Every finance professional knows the struggle of analyzing and retrieving insights out of spreadsheet data. AI simplifies this process by turning numbers into concise, actionable written summaries. With just a few keystrokes, your month-end report can be ready.

Example prompt:

“Summarize the revenue and expense data in this spreadsheet. Highlight any anomalies.”

Spot financial anomalies

AI-powered tools are great at analyzing complex datasets to flag duplicate entries, high-value transactions missing documentation, or irregular patterns in spending. For auditors and accountants, this acts as an efficient second pair of eyes.

Example prompt:

“Identify transactions over $3,000 in this expense report that don’t have a matching purchase order.”

Pro tip: You can even upload your expense policy and a screenshot of a receipt and ask AI to see if the two are compatible. 

Create cash flow forecasts

Analyzing financial projections takes time and expertise, but AI can run the numbers and generate forecast summaries with assumptions clearly outlined.

Example prompt:

“Use the given revenue and expense projections to create a three-month cash flow report.”

HR: AI enhancing recruiting and employee retention

Craft effective job descriptions

Recruiting top talent often starts with an engaging job post. AI can write job listings tailored to specific roles, company culture, and diversity goals, saving recruiters time and improving hiring outcomes.

Example prompt:

“Create a job description for a remote junior software engineer focusing on growth opportunities.”

Develop targeted interview questions

AI supports HR professionals by crafting custom interview questions. Whether you need questions for specific roles or particular skills, AI helps focus the conversation where it matters most.

Example prompt:

“Generate five behavioral interview questions for a project manager emphasizing leadership and adaptability.”

Another pro tip: Upload the job description and a candidate’s resume and have AI spot where the candidate’s skills align and where there could potentially be gaps. It’s still up to you to dig deeper during the interview (don’t outsource your interviewing and people skills), but this can give you some things to think about. 

Summarize employee feedback

Employee satisfaction surveys and performance reviews often include valuable insights, but parsing through endless responses can be overwhelming. AI tools can identify recurring themes and summarize findings, providing actionable insights in minutes.

Example prompt:

“Summarize strengths and challenges mentioned in these employee reviews.”

Create personalized onboarding plans

Effective onboarding is key to retention. AI can help HR teams design tailored onboarding programs by factoring in the employee’s role, location, and team structure. Here’s a more in-depth post on this subject.. 

Example prompt:

“Design a 30-day onboarding plan for a Customer Success Manager  that includes training, shadowing, and performance check-ins.”

Risks and pitfalls to consider while using AI

While AI offers game-changing potential, it’s not without its challenges. Here are some key risks to keep in mind when integrating AI into your business functions.

Hallucinations and errors

AI can sometimes provide inaccurate or overly confident responses, particularly in legal, financial, or compliance scenarios. Always double-check AI-generated outputs to ensure accuracy.

Loss of context

AI tools need precise, well-organized data to deliver meaningful results. Vague or overly general prompts can produce irrelevant or misleading results.

Be detailed in your instructions, and ensure all necessary context is provided.

Data privacy concerns

Many AI tools rely on cloud-based systems, meaning any data you input is stored or processed externally. Avoid pasting sensitive information into tools without clear data privacy policies, or consider enterprise-grade AI solutions with stronger security measures.

Potential bias

AI tools trained on public datasets may unintentionally replicate biases present in the data. Use tools designed for fairness to eliminate potential bias in job descriptions, performance reviews, or customer-facing policies.

Wrap-up

Automation technology like AI doesn’t aim to replace professionals. Rather, it acts as an invaluable assistant. Think of AI as your fastest, most focused assistant, quick to get things moving but still reliant on your expertise for the best results.

By leveraging AI, you can drastically cut down on repetitive tasks, streamline complexity, and empower your team to focus on high-impact work. Transforming departments like legal, finance, and HR has never been easier, or more essential, in staying ahead in today’s fast-paced business world.

What about you? What are your favorite use cases of AI in “the back office”?

ai and human shaking hands

From day one to day 90: Using ChatGPT to support onboarding and continuous learning

Why AI can transform onboarding and training

Onboarding and continuous learning are critical to building a strong, capable workforce, but they can also be time-consuming and inconsistent. New hires often feel overwhelmed due to  information overload. At the same time, managers are stretched thin trying to provide personalized support. Therefore, it’s no surprise that companies are starting to explore ways in which AI can help provide a scalable and accessible way to enhance the onboarding and training experience. This isn’t about replacing human interaction, but about making important information more consistent, approachable, and available on demand. For the purpose of this post, we will focus on ChatGPT.

Instant and personalized knowledge bases

ChatGPT can act as an always-available assistant for new hires, answering common questions about processes, policies, tools, and culture. Instead of waiting hours or days for a manager’s reply, a new team member can ask simple questions such as “How do I submit a PTO request?”, “How do I request help from IT?”, “Who needs to approve external communications before they’re published?” or “What branding guidelines should I follow when creating social media posts?”. Note that it’s easy to train custom versions of ChatGPT by feeding it internal documentation like your handbook and communication playbook, to deliver answers specifically for your company. 

Role-specific learning paths

Managers and HR teams can use ChatGPT to quickly create customized onboarding checklists or learning plans for different roles. For example, you can use a prompt like “Create a 30-day onboarding plan for a new Customer Success Manager for a SaaS company/[your company]”. You can even take it a step further by asking for key success metrics or for further details about a specific objective, for a daily planner that includes recurring meetings like stand-ups, or for a table indicating which tasks involve other team members and which ones are self-guided. 

This approach ensures that every new hire has a thoughtful, structured experience without requiring managers to reinvent the wheel every time.

Practicing scenarios and soft skills

ChatGPT can simulate real-world conversations, giving new hires a chance to practice soft skills in a safe environment. For example:

  • Handling a difficult customer interaction
  • Conducting a feedback conversation with a colleague
  • Asking questions during a discovery call
  • Conducting a Quarterly Business Review (QBR)
  • Managing a customer who missed key onboarding deadlines.

Just provide ChatGPT with instructions like “Act as a customer who…” or “Simulate a situation where…”, or “Pretend to be a user who”. These role-playing exercises help employees build confidence and prepare for real-world challenges before they encounter them.

Reinforce ongoing training

Of course, training doesn’t stop after the first 90 days. ChatGPT can also serve as an ongoing resource for you when it comes to things like

  • Quizzing employees on company values, product knowledge, security protocols, or value proposition
  • Scenario testing, where employees can walk through different case studies and challenges.
  • Microlearning sessions, allowing employees to engage in bite-sized learning at their own convenience.

Here are some examples:

After a new product release, Customer Success Managers could quiz themselves on the new features by using prompts such as “Give me 5 multiple-choice questions about [product]’s new feature rollout.” Or an Account Executive could ask ChatGPT to act as a specific buyer persona and provide feedback on how well the AE explained the value of a specific feature set. You can also use the tool to help prepare for potentially uncomfortable internal conversations. For example, you can ask ChatGPT to “Act as a teammate to whom I need to give critical feedback about their time management skills.”. Examples of microlearning opportunities are a CSM quickly refreshing their knowledge on upcoming feature names before a call with a customer, or a Support Engineer getting a summary of the last 3 releases to help explain to a customer why they should upgrade to the latest version of the product. 

Fostering a culture of continuous learning is not just beneficial for everyone, but it can also be fun. Consider creating a Slack channel where team members discuss creative uses of AI that help them in their roles. 

Support managers and team leads

ChatGPT isn’t just for new hires, but it can also be a valuable tool for the people supporting them. Managers and trainers can use AI to:

  • Get suggestions on how to improve existing training materials
  • Provide ideas for mini-”homework” assignments for each role on the team to continue to sharpen their skills (“Explain our newest feature like you’re talking to a non-technical customer”)
  • Help team members hone their communication skills (for instance, have ChatGPT generate an email from a customer who is frustrated with something specific and then assign the team member the task to respond to it)
  • Reinforce knowledge of new product features, internal tools, or SOPs by having team members quiz themselves (“Summarize the top 2 use cases for marketers and for developers when interacting with X”).

By using ChatGPT, managers can make professional growth feel more continuous and accessible, help employees practice in a safe space, and foster a culture of curiosity, all without adding heavy training costs. It also frees up time spent on repetitive tasks and frees managers up to focus more on mentorship.

These are just a few ideas on how to use ChatGPT to help with onboarding and continuous learning, making it more consistent, accessible, and effective, while allowing managers and team leads to have more time for individual coaching. By combining the best of human guidance with the capabilities of AI, organizations can create a better experience for everyone involved.

What about you? What are your ideas for using ChatGPT for onboarding and ongoing training?

Diversity in diversity

My previous post outlined some thoughts to consider when hiring career changers. One of the benefits of this approach is that you’re bringing fresh perspectives to your company. If you limit your team to individuals who have only worked in your industry, you’re missing out. Of course, relevant experience is highly valuable, but so is diversity and a rich set of experience, which is why more organizations are moving away from the concept that “cultural fit” means building a hyper homogenous company.

Education

Even just a few years ago, having a degree from a prestigious university was considered a massive advantage. Don’t get me wrong – graduating through a rigorous program is no small feat and should be rewarded. But don’t discount someone who might have been a late bloomer, someone who simply didn’t have the financial means to go to an ivy league school, or whose life circumstances just took them in a different direction. Don’t discount the non-traditional learner. We recently hired one, and he’s got all the hustle, attitude and smarts needed to excel. 

Career paths

Some people know early on what they want to be. And of course, you have to admire someone who clearly has a passion for a specific field. Not to mention that for certain roles, it’s important that a candidate has had a clear and steady career trajectory. For other positions, you may be able to widen the pool of applicants. Don’t just look at the hard skills required, but also the soft skills, such as communication skills, impeccable time management, a high degree of emotional intelligence and adaptability, and the ability to provide outstanding customer service. 

Levels of experience

Let’s be honest – ageism is real. Yes, we can call the more mature candidates “overqualified”, but why wouldn’t you hire someone who is so qualified that they will allow you to raise the bar? Aren’t you sick of hearing about the boomer versus millennial versus Gen Z battles? You’re doing your employees a disservice if they don’t get a chance to work with individuals from different generations and with different levels of professional experience. In fact, offering diversity across generations is the only way to create an environment that mimics the “real world” – and your customers’ world!

Cultural backgrounds

One of the biggest gifts that you can give your employees is the ability to be immersed in a stimulating environment that fosters open-mindedness, provides a multitude of perspectives, and is a microcosm of the diversity that makes us better. Every individual, regardless of their background, brings a unique perspective to your organization. Leverage this, provided that the person embodies your company values and has the aptitude to succeed in their role (and that you have the willingness and bandwidth to train them!). 

Our founder, David Cummings, recently published a blog post about how certain challenging life experiences can be an important characteristic for an entrepreneur. I couldn’t agree more. I’ll add to this the struggle of being an outsider due to ethnic, social, or economic background, physical challenge, gender, or any of the factors outlined above. And if you’re looking for an entrepreneurial spirit in all of your employees, keep that in mind.

One of the most important things to consider when hiring is your company’s core values and how a candidate embodies them. For us, it’s being adaptable, scrappy, positive, supportive, self-starting, to focus on the things we can control, and to put our customers first are what matters most. And that’s what we’re looking for when recruiting. If your main focus is to hire great people, you will likely have a more diverse team.  

What about you? What are your thoughts on organically fostering diversity by hiring the best people and giving them a chance, regardless of their background?

Hiring career changers

Since the outbreak of the pandemic more than two and a half years ago, people have been quitting their jobs at a never before seen rate. Last year, more than 47 million people left their employers in order to pursue something new. Many of these seekers are looking for a career change. At Hannon Hill, we have been fortunate to be able to hire several of them, and they’ve already made a huge positive impact. As we’ve said before, “you can teach someone how to do something, but you can’t teach them how to be”. If you come across someone with a great attitude, strong work ethic, and some of the other traits that you deem important, consider giving them a chance, even if they don’t have some of the role specific experience that you were looking for. Here are some thoughts to consider in order to make sure that you’re setting those new hires up for success.

Don’t rush the hiring process

Hiring a new team member is a monumental decision, not just because the wrong fit can damage your company culture and lower morale, but also because the individual trusts you with their career and their livelihood. You want to be sure that the candidate really wants the job, that they have a realistic picture of what’s expected and what joining the company will be like, that they have the aptitude to excel, and that they are an exceptional fit. Most of the time, it’s impossible to make this determination after just one interview. Don’t rush into a hire just to fill the position or for fear of missing out on a candidate. 

Be sure that you’re equipped to train them

Every new employee deserves a top notch onboarding experience, but it’s even more crucial for career changers. No matter how self-starting someone is, they will need proper training. If their manager and their team members don’t have the time to invest in thorough knowledge transfer, you’re likely not setting yourself or the career changer up for success. In addition to providing on the job training, make resources like online courses and books available, and, whenever possible, help them find a mentor.

Note that the training also needs to cover how your organization works. Sometimes, it’s not just a new skill set and job that the new employee is learning, but a whole new environment and organizational structure. You can’t expect acclimation to happen overnight, and you need to ease them into this new way of working. One of our most recent hires is a former teacher who had not worked in the corporate world. Imagine what a big change this was for her! (BTW, she is doing great!)

Plan to fill knowledge gaps

Don’t rely on the new person to figure out what they need to learn and how they’ll acquire the necessary knowledge and skills. Collaborate with them to clearly identify how and when the knowledge gaps will be filled, and set benchmarks so you both can see if things are moving in the right direction. Encourage complete honesty. What do they feel confident or excited about? What is causing apprehension? Where do they think they can make a big impact? What is their preferred method of learning? Also note that honesty goes both ways. Be realistic about expectations, professional development and potential career trajectories. Don’t overpromise. 

Provide immersive onboarding

One aspect of learning how your company works involves learning the inner workings of each department. That’s where an immersive onboarding experience is quite valuable. Schedule time for the new hire to shadow team members in other departments and to have Q&A sessions. Some learning can be done by osmosis, by listening to calls with customers and prospects or overhearing conversations between co-workers. Of course, this is much harder to do in a remote only environment. You should also consider some scheduled cross-departmental learning and “getting to know each other”s. 

Be open to new perspectives, and encourage input

By bringing someone from a different background into your organization, you are giving yourself an excellent opportunity to listen to fresh perspectives. Encourage your new hires to share their first and second impressions, as well as any new ideas they may have. Just because you’re new doesn’t mean that you shouldn’t speak up. Some of the best innovations and ideas come from looking outside your industry. 

Ditch the acronyms

Be mindful of the fact that not everyone knows what an SOW, RFP, or PO is, let alone know the specific technical terminology that you use in your products. Get into the habit of speaking in terms that everyone can understand, as it will make your company more inclusive to your team members, customers, and prospects. Also: if you must make inside jokes, explain them to the new hires.

Check in regularly

Quality onboarding does not happen in a week. Check in with your new hires regularly, especially when they’re career changers. What’s been going well? Do they feel that you’ve held up your end of the bargain? Note that those check ins don’t always have to be scheduled. Sometimes a simple “how are things going?” when stopping at their desk can be just as effective. 

Not all positions lend themselves to hiring career changers with little or no experience in the field, but please don’t discount someone who is looking to make a change if they are great cultural fits, have a strong drive, and the right aptitude and soft skills. You could be missing out on gems. That said, not every company is prepared for those types of hires. That’s why transparency on both sides is so crucial.

What about you? What are your thoughts on hiring career changers?

7 signs that a candidate is not prepared

The result of a successful interview is not necessarily a new hire. It’s knowing if a candidate is or isn’t a good fit for your company. Since better interviews lead to better hires (as you’re weeding out the individuals who are not a fit), it’s important that you always strive to become a better interviewer and that you are prepared for each interview. You know how to strike the right balance between asking common questions in order to compare candidates and being adaptable enough to dig deeper when necessary to have a meaningful and organic conversation. Furthermore, you are able to instantly identify a candidate who is not appropriately prepared. How? Let’s take a look. 

They didn’t bring their resume

When a candidate has an in-person interview, they should bring copies of their resume for each interviewer as a courtesy instead of expecting the interviewers to either have it memorized or printed themselves. Ideally, they also bring other supporting documents, such as references and any pertinent samples of their work (for instance, a marketing candidate might bring a brochure that they created). 

They don’t have a good reason why they want to work for your company

“How did you find out about the position?” is a slowball and a way to make candidates feel comfortable. Generally, if someone is excited about the opportunity at your company, they remember how they learned about it. If someone says “It might have been [insert website here]”, make a mental note to ask more about their job hunting processes. How do they identify companies that they want to work for? Which brings us to the next red flag. If a candidate can only give you generic reasons, they may not have investigated your company much prior to the interview. If the response is “you seem to have a great company culture”, probe further and ask “What does culture mean to you?” and “How would you describe our culture?” Listen carefully. If the answer mostly revolves around a relaxed dress-code or the “laid back” environment, there may be a misalignment. 

They can’t explain your products and/or services

I like to ask our candidates what they did to prepare for the interview. You’d be surprised at some of the answers. Believe it or not, some individuals responded to the effect of “not much”, or “I poked around on your website”. Find out if the candidate downloaded your whitepapers or signed up for a trial of your product if available. Have them explain your offerings and your value proposition. Depending on the seniority of the position, consider asking the candidate strategic questions such as “what other verticals do you think might be good fits for us?” or “what do you think is keeping our prospects up at night?”.

They don’t know who the interviewers are

One of the most obvious signs that someone is not prepared for an interview is when they don’t know with whom they’re interviewing. Make sure that your HR rep who set up the interview gives the candidate the names and titles (not email addresses – you want to make sure that the candidate is resourceful enough to find them when sending follow-up emails) of each person with whom the candidate will speak. If someone clearly does not remember who they’re talking to and didn’t take the initiative to even write down pertinent information in preparation for the interview, it’s a reason for concern. Some interviewees demonstrate their level of preparedness through comments, such as “I saw that you went to [school]/used to work for [company]”, “So you started out in [department]”, or “I read on your blog that”. Good! But others may be more reserved, so you may just ask them “What do you know about [name of person]?”

They only talk in generalities

A decent candidate proactively researches what types of questions are typically asked in interviews for the position that they’ve applied for. A good candidate is prepared to answer these questions in a thoughtful manner that includes very specific, personal examples. For instance, if the question “Tell me about a time when you went through extraordinary lengths to (close a deal, make a customer happy)”, is only met with general statements (“You have to go the extra mile, and customer service is what I do best”), the interviewee may not have been appropriately prepared.

They can’t answer this crucial question

You want people on your team who are invested in their own professional development. Consider asking something along the lines of “What do you do to get better at your craft?” or “Who is a thought leader in your field that you follow?”. If you catch a candidate off-guard and they can’t name any blogs or books they read, podcasts they listen to, or courses that are being offered, it should give you pause. Not everybody can think quickly on their feet in a stressful situation such as an interview. However, a well prepared candidate may have expected this question.

They don’t ask thoughtful questions

The types of questions that a candidate asks during the interview are just as important as the answers they give – sometimes even more important, as they are a direct reflection of the person’s interest in the position and genuine desire to learn about your expectations, your challenges, and vision. They also reveal critical thinking skills and the candidate’s willingness to identify if and how this could be a mutually beneficial relationship. If the interviewee doesn’t take advantage of having the opportunity to ask questions and or just inquires about benefits and work hours, it’s generally not a great sign. 

Understand, though, that you simply can’t apply the same expectations to all candidates. If you offer an entry level position for recent graduates, you can’t expect the candidates to go through the same preparation process as candidates for a senior Account manager, for example. In addition, the further along in the vetting process someone is, the more preparation you should expect. 

Finally, note that even if a candidate aced the interview, you still want to be thorough in your process and not skip any steps, such as waiting for the follow-up, having them do an assessment with deliverables that are relevant to the position, and a cross-departmental interview to determine culture fit. Fast-tracking a candidate can be one of the biggest (and most expensive) pitfalls when it comes to hiring

What about you? How do you determine if a candidate is not adequately prepared for an interview?