Find Work Worth Doing takes you on the journey to create meaningful work that meets your unique talents and strengths. It is the modern career strategy guide for anyone looking to grow, change, or reinvent their work by covering every aspect of a job seeker’s needs from the foundations of career management, crafting a personalized vision of success, through the technical details of a job search. Working through the activities and tips on writing a resume, searching for job openings, and preparing for an interview gives readers the edge in the modern job market. By recognizing each person’s unique definition of success, it helps you build your plan for fulfillment and job satisfaction.

Go beyond simply earning a paycheck to find work that excites you and makes you want to get up each day with a sense of mission and purpose.

More of his writing can be found on his Subtack “Herding Cats”

Technology Training

Not everyone needs a certification. Most people just need someone to sit down, explain the thing in plain language, and give them the confidence to stop dreading their inbox, their settings menu, or the next “reply all.” These sessions fill that gap in a practical, jargon-free, and scalable way, from a single team to a full staff training day.

Productivity with Microsoft 365

Most people use maybe 20% of what’s already sitting on their desktop. This session walks through the everyday features of Outlook, Word, Excel, and Teams that actually save time — the shortcuts, templates, and settings that turn “I’ve always done it this way” into “why didn’t I know this sooner.”

Best for: Teams that already have Microsoft 365 and want to get the most out of it.

Introduction to AI

A grounded, no-hype look at what generative AI tools actually do, where they help, and where they don’t. Attendees leave with a working understanding of the technology, a few tools worth trying, and enough judgment to use them responsibly.

Best for: Teams and individuals who feel behind on AI and want a clear starting point, not a sales pitch.

How to Use LinkedIn

LinkedIn is more than a digital resume, but most people only use it that way. This session covers building a profile that actually represents you, using the platform to stay visible in your field, and networking without it feeling forced or transactional.

Best for: Job seekers, professionals building their personal brand, and anyone who’s had a LinkedIn account for years without really using it.

Cyber Security / Staying Safe Online

The threats that actually catch people aren’t the sophisticated ones — they’re the convincing email, the reused password, the “urgent” text from the bank. This session covers the everyday habits that close most of the gap between an organization and a breach.

Best for: Any team that uses email, which is every team.

Digital 101: Understanding Everyday Technology

A foundational session for anyone who wants to feel more confident with the technology they use every day — devices, apps, cloud storage, basic troubleshooting — without the assumption that everyone already knows the vocabulary.

Best for: Staff or community members who didn’t grow up with this technology and want a patient, judgment-free starting point.

PEBKAC: How to Solve Your Computer Issues Before They Start

Most tech support calls trace back to the same handful of preventable habits. This session teaches the basic troubleshooting and maintenance skills that keep small problems from becoming IT tickets and builds the confidence to solve them without calling for help.

Best for: Organizations trying to cut down on routine help desk requests, and anyone tired of feeling helpless when something goes wrong.

Group Training

Every team has the same handful of friction points: unclear communication, unmotivated meetings, managers who were never taught to manage. These sessions target those points directly, built from real workplace experience rather than theory, and scaled to fit anything from a leadership offsite to an all-staff training day.

From Boss to Coach: How to Coach Teams and Employees

Managing tasks and developing people are two different skills, and most new managers are taught only the first. This session covers the shift from directing to coaching—how to ask better questions, give feedback that lands, and build a team that grows instead of just executing.

Best for: New and mid-level managers making the leap from doing the work to leading the people who do it.

Painless Presentations: How to Make Better Slide Decks

Bad slides aren’t a design problem; they’re a thinking problem. This session covers how to structure a deck around a point instead of a pile of information, and the handful of design habits that make the difference between a slide people read and one they listen to.

Best for: Anyone who has to present to a boss, a board, or a client and wants their slides to help, not hurt.

Zero Nuance in Text: Writing Clearly and Cleanly

Most workplace confusion isn’t a communication failure; it’s a writing failure. This session covers how to write emails, messages, and documents that say exactly what you mean, cut the hedging, and leave no room for the reader to guess what you actually want.

Best for: Teams drowning in back-and-forth clarifying emails and Slack threads.

CX Plus: Customer Service That Creates Fans

Adequate customer service keeps people from leaving. Great customer service turns them into advocates. This session covers the mindset and practical habits that move a team from handling requests to creating the kind of experience customers talk about.

Best for: Customer-facing teams that want to differentiate on experience, not just resolve tickets.

The Generation Myth: Better Ways to Bridge the Age Gap

Generational labels explain less than most people think, and they’re a poor substitute for actually understanding your colleagues. This session moves past the stereotypes and into what actually drives friction across a multigenerational team and how to close it.

Best for: Teams where generational tension is getting blamed for problems that are really about communication and expectations.

How Did You Feel: Adding Magic to Your Leadership Approach

The best leaders people remember aren’t remembered for their strategy decks. This session digs into the emotional and relational side of leadership and the moments, gestures, and habits that build the kind of loyalty a title alone can’t buy.

Best for: Leaders who are technically strong but want their teams to feel something, not just comply.

No Want Ads: How to Proactively Attract the Talent You Need

Waiting for good applicants to find a job posting is a losing strategy in a tight market. This session covers how to build a pipeline, a reputation, and a network that brings talent to you before you’re desperate to fill a seat.

Best for: Organizations tired of reactive hiring and ready to build a real talent strategy.

Discovering & Applying Strengths in the Workplace

Most performance problems aren’t a skills gap, they’re a fit gap. This session introduces a strengths-based approach to understanding what each person on a team naturally does well, and how to put people in positions where that talent actually shows up in results.

Best for: Teams and leaders looking to build on what’s already working instead of only fixing what’s broken.

Herding Cats: Creating a Coaching Culture

A coaching culture doesn’t happen because one manager reads a book. It happens when coaching becomes the default way a team talks to each other, at every level. This session covers what that actually takes to build and sustain across a whole organization.

Best for: Leadership teams ready to move coaching from an individual skill to an organizational habit.

Work Worth Doing: Tracking Your Development

Professional growth rarely happens by accident. This session gives individuals a practical framework for tracking their own development, naming what “worth doing” means for them, and building a career that reflects it rather than just reacting to whatever comes next.

Best for: Professionals who want ownership of their own growth instead of waiting for someone else to plan it.

Understanding Human Motivation & Engagement

Most engagement strategies treat people as one type of person. This session breaks down what actually drives motivation, why the same incentive lands differently across a team, and how leaders can tailor their approach instead of guessing.

Best for: Leaders and HR teams trying to move the needle on engagement scores that haven’t budged.

Professional Skills Development: What, Why, and How

The skills that keep careers moving forward rarely show up on a job description. This session names the durable, transferable skills that matter most, why they’re often overlooked, and how individuals and organizations can build them intentionally.

Best for: Organizations building a professional development program, and individuals who want a clearer picture of what to work on next.

Let’s talk about what your team needs

Every session starts with a conversation about your group and what you’re actually trying to shift. If you’re not sure which topic fits, or want something built to spec, that’s exactly the conversation to have first.

Fractional Technology Solutions

All organizations have information technology, and many, especially those without a dedicated PMO or IT Manager, need someone who can plan initiatives, run day-to-day delivery, manage vendors, and facilitate cross-team decisions, without needing a full-time staff person.

Circle City Consulting offers service-focused solutions to close your technology gaps.

We offer experienced support and management options with a flexible scope to meet your mission, including advisory consulting, fractional hands-on project work, part-time retained staffing, and temporary/interim headcount. The engagement is accountable for outcomes and day-to-day execution, embedded in your team’s operating rhythm, not a report handed off from the outside.

Areas of Focus:

• Digital Strategy Consulting & Planning Facilitation
• Group and Individual User Training (ILT/VILT)
• Disaster Recovery & Business Continuity Planning
• Disaster Recovery & Business Continuity Planning
• Vendor/Contractor Oversight
• IT Project & Program scope, planning, and management
• Technology Audit, Policy Creation, & Documentation
• Workflow & Process Creation
• Instructional Content for ongoing training/support
• Security review and remediation consulting
• RFP/RFQ coaching & review

Who this is for:

> Organizations without dedicated technology management staff

> IT staff juggling multiple vendors without a single point of ownership

> Leaders who need someone to run point on delivery without a full-time hire

> One-time initiatives (e.g. migration, vendor consolidation, upgrades)

> Ongoing part-time coverage outside of break-fix

> Anyone needing a skilled, outside “honest broker” for guidance

Connect with Jason for a customized proposal that fits your needs.