Cliff Redmond Character Analysis: The HR Analyst with a Conscience

Overview

Cliff Redmond enters Supershops Inc. as a fresh HR analyst, armed with video‑game trinkets, a sugary donut box, and an earnest desire to connect. Beneath the plaid shirts and easy smile, he carries the weight of a job that forces him to police colleagues while genuinely wanting to help them. In I Hope This Finds You Well, Cliff becomes both the unwitting enabler of Jolene’s surveillance and her most steadfast anchor—a contradiction that drives his emotional arc and the novel’s exploration of deception and its consequences.

Plot Role: The Unlikely Anchor

Cliff’s first official act is installing monitoring software on Jolene’s computer (Chapter 2), a move that accidentally gives her access to the entire company’s email. He later attempts to smooth over the tension with boat metaphors and butter‑pretzel offers (Chapter 6), revealing a man who believes in process over suspicion. Yet as the story unfolds, Cliff repeatedly crosses the line between HR officer and friend: he offers Jolene rides home (Chapter 9), shares milkshakes at Angels Café (Chapter 16), and even writes “Robin Winters” on a napkin during a darkly humorous murder‑choice game. Each act deepens their bond while tightening the ethical knot. By the novel’s end, Cliff resigns from Supershops to work on employee‑advocacy projects in Calgary—a decision that frees him to pursue a life aligned with his values (Chapter 50).

Motivations and Traits

Cliff is driven by a need to be good at what he does—but “good” for him means seeing the person behind the file. He tells Jolene he hates firing people and copes by pretending they “died” (Chapter 32). He is motivated by family loyalty: he moved back to Calgary to care for his grandmother and returns to his old company partly to stay near her (Chapter 50). His traits—openness, awkward sincerity, a willingness to listen—make him stand out in the toxic Supershops culture. In Chapter 12, he brings mini donuts to the floor and endures stares; his shoulders slump when no one thanks him, yet he persists. Cliff is also riddled with guilt, both about his role in layoffs and about his feelings for Jolene, which he tries to suppress because she is an employee.

Chronological Arc

Cliff’s journey moves from naive optimism to weary realism and finally to purposeful action. Early in the narrative, he believes a few friendly gestures can fix a broken culture (Chapter 6). After firing Larry and getting punched, he admits the guilt “can change you forever” (Chapter 32). Midway, he attempts to distance himself from Jolene by offering her a new HR contact, but her plea that he is “the only one who wanted to give me a chance” makes him reconsider (Chapter 32). The turning point comes when Jolene urges him to quit—arguing that “taking care of yourself is important” (Chapter 43). By the epilogue, Cliff has left HR at Supershops to help employees organize, and he meets Jolene as an equal, shaking hands on a future of honesty (Chapter 50).

Relationships

With Jolene Smith: The core of his arc. Cliff starts as her monitor, becomes her ride‑share companion, then her confidant. His growing affection battles with professional boundaries; after the kiss in the car, he tries to reassign her but gives in (Chapter 32). Their late‑night texts (“Milkshakes?”) and the final handshake show a relationship built on mutual healing rather than romance.

With coworkers: Caitlin and Garret dismiss him as “HR” (Chapter 10). Armin barely acknowledges him. Rhonda, the office administrator, is indifferent—but Cliff still tries. He is socially isolated in the office, which makes his connection with Jolene more precious.

With his grandmother: He was raised by her in a low‑income area (Chapter 16) and moved back to Calgary when she fell ill. Her recovery allows him to pursue his advocacy work.

Key Decisions and Consequences

Themes and Symbols

Cliff embodies the theme of empathy across differences . He grows up in a low‑income neighborhood raised by a grandmother; Jolene comes from a strict immigrant family. Their shared vulnerability bridges the gap. Workplace toxicity and surveillance is literal through Cliff’s job, but his moral struggle shows that even a “good” HR person can perpetuate harm. The Tiger‑Tastic milkshake (Chapter 16) becomes a symbol of trust—the first time Jolene lets down her guard. His car, smelling of old dog and New Car Smell air freshener (Chapter 9), is a sanctuary where rules loosen and honesty starts.

Five Key Questions

1. Why does Cliff install surveillance software on Jolene’s computer?
He is acting on management’s orders after her white‑font email incident. He believes it is a routine disciplinary measure and does not anticipate the privacy breach it causes.

2. What does Cliff’s “murder choice” napkin reveal about his personality?
When Jolene pushes him to name a coworker he would hypothetically “off,” he writes “Robin Winters” because of petty annoyances (reply‑all thanks, long bathroom breaks). The joke shows his willingness to be silly with Jolene and his trust in her secrecy.

3. Why does Cliff continue carpooling with Jolene after the surveillance scandal?
He admits he enjoys her unpredictability and finds her “more interesting” than anyone else (Chapter 16). The rides become a routine escape from his lonely HR role.

4. What leads Cliff to finally leave Supershops?
Jolene directly tells him to quit, pointing out that his guilt over firings is poisoning him (Chapter 43). Combined with a job offer from his old company in Vancouver—which he adapts to stay in Calgary—he chooses a path aligned with his ethics.

5. How does Cliff’s relationship with Jolene change by the epilogue?
After she confesses her feelings via letter, they meet for milkshakes, kiss, but agree to remain friends while she works on herself. By Rhonda’s retirement party a year later, they share a handshake and a plan to meet for advice—a foundation built on honesty rather than obligation.

For more detail on the story’s resolution, see the ending explained and the questions and answers page.